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Journal articles on the topic 'RCM (Ring closing metathesis)'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Krehl, Stefan, Diana Geißler, Sylvia Hauke, Oliver Kunz, Lucia Staude, and Bernd Schmidt. "The catalytic performance of Ru–NHC alkylidene complexes: PCy3 versus pyridine as the dissociating ligand." Beilstein Journal of Organic Chemistry 6 (December 15, 2010): 1188–98. http://dx.doi.org/10.3762/bjoc.6.136.

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The catalytic performance of NHC-ligated Ru-indenylidene or benzylidene complexes bearing a tricyclohexylphosphine or a pyridine ligand in ring closing metathesis (RCM), cross metathesis, and ring closing enyne metathesis (RCEYM) reactions is compared. While the PCy3 complexes perform significantly better in RCM and RCEYM reactions than the pyridine complex, all catalysts show similar activity in cross metathesis reactions.

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2

Massé, Paul, Sabine Choppin, Lucia Chiummiento, Gilles Hanquet, and Françoise Colobert. "Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-Metacyclophane." Synlett 31, no. 06 (November 29, 2019): 559–64. http://dx.doi.org/10.1055/s-0039-1691523.

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A convergent approach for the synthesis of (±)-myricanol, a strained diarylheptanoid isolated from Myricacae, was undertaken using a Suzuki–Miyaura coupling followed by a ring-closing metathesis (RCM). Herein, we report the unintentional formation of a 26-membered macrocycle as RCM product resulting from a head-to-tail dimerization of the seco-precursor, even in relay ring-closing metathesis (RRCM) conditions.

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3

Gleeson, Ellen C., W. Roy Jackson, and Andrea J. Robinson. "Ring closing metathesis of unprotected peptides." Chemical Communications 53, no. 70 (2017): 9769–72. http://dx.doi.org/10.1039/c7cc04100d.

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4

Li, Ying, Yugang Bai, Nan Zheng, Yang Liu, Gretchen A. Vincil, Benjamin J. Pedretti, Jianjun Cheng, and Steven C. Zimmerman. "Crosslinked dendronized polyols as a general approach to brighter and more stable fluorophores." Chemical Communications 52, no. 19 (2016): 3781–84. http://dx.doi.org/10.1039/c5cc09430e.

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Fluorescent, aqueous-soluble, crosslinked dendronized polyols (CDPs) are obtained through a sequential process involving ring-opening metathesis polymerization (ROMP), intra-chain ring-closing metathesis (RCM), and hydrolysis.

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5

Domon, Daisuke, Kenshu Fujiwara, Natsumi Kawamura, Ryo Katoono, Hidetoshi Kawai, and Takanori Suzuki. "A New Variant of Fused Cyclic Ether Synthesis Based on Ireland-Claisen Rearrangement and RCM." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800718.

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A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement of a ( Z)-3-alkoxyprop-2-en-1-yl glycolate ester having a cyclic ether on the oxygen at C3 of the ( Z)-prop-2-en-1-yl group stereoselectively produced an anti-α,β-dialkoxyester which was successfully transformed to a fused bicyclic ether via a reaction sequence including RCM.

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6

Schultze, Christiane, and Bernd Schmidt. "Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins." Beilstein Journal of Organic Chemistry 14 (December 5, 2018): 2991–98. http://dx.doi.org/10.3762/bjoc.14.278.

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8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.

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7

Siano, Vincenzo, Ilaria D’Auria, Fabia Grisi, Chiara Costabile, and Pasquale Longo. "Activity and stereoselectivity of Ru-based catalyst bearing a fluorinated imidazolinium ligand." Open Chemistry 9, no. 4 (August 1, 2011): 605–9. http://dx.doi.org/10.2478/s11532-011-0034-6.

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AbstractGrubbs II generation catalyst (3), bearing a fluorinated imidazolinium ligand, was investigated in cross metathesis (CM), ring closing metathesis (RCM) and ring opening polymerization metathesis (ROMP) for a variety of substrates. Kinetic studies showed reduced stability of the catalyst in methylene chloride following the first 15 minutes of reaction preventing a higher efficiency despite the very high activity. Beneficial solvent effects on the catalyst stability were observed by performing RCM in C6F6.

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8

Liniger, Marc, Christian M. Neuhaus, and Karl-Heinz Altmann. "Ring-Closing Metathesis Approaches towards the Total Synthesis of Rhizoxins." Molecules 25, no. 19 (October 2, 2020): 4527. http://dx.doi.org/10.3390/molecules25194527.

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Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ring-closure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.

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9

Chatterjee, A. K., F. D. Toste, S. D. Goldberg, and Robert H. Grubbs. "Synthesis of coumarins by ring-closing metathesis." Pure and Applied Chemistry 75, no. 4 (January 1, 2003): 421–25. http://dx.doi.org/10.1351/pac200375040421.

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Investigations into olefin ring-closing metathesis (RCM) have led to a general method for the synthesis of coumarins. Catalysts with higher activity, such as the second-generation ruthenium catalyst, promote the intramolecular reaction between two-electron deficient olefins. This method allows for convenient access to a variety of coumarins substituted at both the 3- and 4-positions, as well as a tetrasubstituted example.

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10

Masuda, Shun, Shugo Tsuda, and Taku Yoshiya. "Ring-closing metathesis of unprotected peptides in water." Organic & Biomolecular Chemistry 16, no. 48 (2018): 9364–67. http://dx.doi.org/10.1039/c8ob02778a.

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11

Setaka, Wataru, Sayaka Higa, and Kentaro Yamaguchi. "Ring-closing metathesis for the synthesis of a molecular gyrotop." Org. Biomol. Chem. 12, no. 21 (2014): 3354–57. http://dx.doi.org/10.1039/c4ob00470a.

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12

Kotha, Sambasivarao, Milind Meshram, Priti Khedkar, Shaibal Banerjee, and Deepak Deodhar. "Recent applications of ring-rearrangement metathesis in organic synthesis." Beilstein Journal of Organic Chemistry 11 (October 7, 2015): 1833–64. http://dx.doi.org/10.3762/bjoc.11.199.

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Ring-rearrangement metathesis (RRM) involves multiple metathesis processes such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) in a one-pot operation to generate complex targets. RRM delivers complex frameworks that are difficult to assemble by conventional methods. The noteworthy point about this type of protocol is multi-bond formation and it is an atom economic process. In this review, we have covered literature that appeared during the last seven years (2008–2014).

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13

Dumeunier, Raphaël, Thomas Gregson, Somhairle MacCormick, Hiroki Omori, and Eric J. Thomas. "Some limitations of an approach to the assembly of bryostatins by ring-closing metathesis." Organic & Biomolecular Chemistry 15, no. 13 (2017): 2768–83. http://dx.doi.org/10.1039/c7ob00079k.

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14

Kiss, Loránd, Márton Kardos, Csaba Vass, and Ferenc Fülöp. "Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives." Synthesis 50, no. 18 (July 26, 2018): 3571–88. http://dx.doi.org/10.1055/s-0036-1591600.

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Because of their biological relevance, cyclic β-amino acids have generated increasing interest and had significant impact in drug research over the past two decades. Their preparation and further functionalization towards new types of molecular entities have received large interest in synthetic and medicinal chemistry. Various types of metathesis reactions, such as ring-opening (ROM), ring-closing (RCM), or cross metathesis (CM) are used widely for access to either alicyclic β-amino acids or other densely functionalized derivatives of this group of compounds. This account intends to provide an insight into the most relevant synthetic routes to this class of derivatives with the application of metathesis reactions. The review focuses on the presentation of selective and stereocontrolled methodologies in view of versatility, robustness, limitations and efficiency.1 Introduction2 Synthesis and Transformation of Cyclic β-Amino Acids through Metathesis Reactions2.1 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Ring-Closing Metathesis2.2 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Cross Metathesis2.3 Synthesis of β-Amino Acids with Larger Ring Systems by Ring- Closing Metathesis2.4 Synthesis of β-Amino Acids with Condensed Ring Systems by Ring-Rearrangement Metathesis2.5 Stereocontrolled One-Step Synthesis of Functionalized Cispentacin and Transpentacin Derivatives2.5.1 Stereocontrolled Synthesis of Functionalized Cispentacin and Transpentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acid Derivatives2.5.2 Stereocontrolled Synthesis of Functionalized Azetidinones and β-Amino Acid Derivatives from Condensed Ring β-Lactams by Ring-Opening Metathesis2.5.3 Carbon–Carbon Double Bond Functionalization of β-Amino Acid Derivatives and β-Lactams with α,β-Unsaturated Carbonyl Compounds through Cross Metathesis2.5.4 Synthesis of Functionalized β-Amino Acid Derivatives and β-Lactams through Chemoselective Cross Metathesis3 Conclusions and Outlook

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15

Schmidt, Bernd. "Connecting catalytic cycles by organometallic transformations in situ: Novel perspectives in the olefin metathesis field." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 469–76. http://dx.doi.org/10.1351/pac200678020469.

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Tandem sequences consisting of an olefin metathesis step and a subsequent non-metathesis reaction become accessible by organometallic transformations of the Ru-carbene species in situ. This contribution highlights some tandem sequences that rely on the conversion of the metathesis catalyst to Ru-hydrides, with special emphasis on the tandem ring-closing metathesis (RCM)-double-bond isomerization sequence.

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16

Kotha, Sambasivarao, Ajay Kumar Chinnam, and Rashid Ali. "Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.02,6]undeca-3,11-dione and its congeners via ring-closing metathesis." Beilstein Journal of Organic Chemistry 11 (July 6, 2015): 1123–28. http://dx.doi.org/10.3762/bjoc.11.126.

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We have developed a simple methodology to transform cis-syn-cis-triquinane derivative 2 into the diindole based macrocycle 6 involving Fischer indolization and ring-closing metathesis (RCM). Various spiro-polyquinane derivatives have been assembled via RCM as a key step.

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17

Schmid, Thibault E., Florian Modicom, Adrien Dumas, Etienne Borré, Loic Toupet, Olivier Baslé, and Marc Mauduit. "Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand." Beilstein Journal of Organic Chemistry 11 (September 3, 2015): 1541–46. http://dx.doi.org/10.3762/bjoc.11.169.

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A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3-bis(2-6-diisopropylphenyl)imidazolidin-2-ylidene) demonstrated excellent latent behaviour in ring closing metathesis (RCM) reaction and could be activated in the presence of a Brønsted acid. The versatility of the catalyst 4a was subsequently demonstrated in RCM, cross-metathesis (CM) and enyne metathesis reactions.

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18

Jacques, Reece, Ritashree Pal, Nicholas A. Parker, Claire E. Sear, Peter W. Smith, Aubert Ribaucourt, and David M. Hodgson. "Recent applications in natural product synthesis of dihydrofuran and -pyran formation by ring-closing alkene metathesis." Organic & Biomolecular Chemistry 14, no. 25 (2016): 5875–93. http://dx.doi.org/10.1039/c6ob00593d.

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19

Reddy, A., and Gowravaram Sabitha. "First Total Synthesis of Cryptopyranmoscatone A3 and Cryptopyranmoscatone B4." SynOpen 02, no. 01 (January 2018): 0058–63. http://dx.doi.org/10.1055/s-0036-1591931.

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The first total synthesis of cryptopyranmoscatones A3 and B4 has been accomplished from d-ribose or but-3-ynol. The key steps involved in the synthesis are oxa-Michael addition, highly diastereoselective Brown allylation, and ring closing metathesis (RCM) and cross metathesis (CM) reactions.

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20

Arisawa, Mitsuhiro, Chiaki Kato, Hiroaki Kaneko, Atsushi Nishida, and Masako Nakagawa. "Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM)." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (2000): 1873–76. http://dx.doi.org/10.1039/b002117m.

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21

Kotha, Sambasivarao, Subba Cheekatla, and Darshan Mhatre. "Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System." Synthesis 49, no. 24 (November 23, 2017): 5339–50. http://dx.doi.org/10.1055/s-0036-1591726.

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The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

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22

Borguet, Yannick, Guillermo Zaragoza, Albert Demonceau, and Lionel Delaude. "Ruthenium catalysts bearing a benzimidazolylidene ligand for the metathetical ring-closure of tetrasubstituted cycloolefins." Dalton Transactions 44, no. 21 (2015): 9744–55. http://dx.doi.org/10.1039/c5dt00433k.

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Second-generation ruthenium–alkylidene complexes featuring the 1,3-di(2-tolyl)benzimidazol-2-ylidene ligand (BTol) are highly efficient catalysts for the synthesis of tetrasubstituted cycloolefins via ring-closing metathesis (RCM).

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23

Chavan, Subhash P., Prakash N. Chavan, and Lalit B. Khairnar. "A concise synthetic approach toward tamiflu (oseltamivir phosphate): cis-aziridine as the key synthon and RCM." RSC Adv. 4, no. 22 (2014): 11417–19. http://dx.doi.org/10.1039/c3ra47210h.

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The key synthon cis-aziridine has been efficiently utilised for the synthesis of tamiflu (oseltamivir phosphate), using Wittig olefination, Barbier addition, Mitsunobu reaction and ring closing metathesis (RCM) as key essentials.

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24

Polyanskii, Kirill B., Kseniia A. Alekseeva, Pavel V. Raspertov, Pavel A. Kumandin, Eugeniya V. Nikitina, Atash V. Gurbanov, and Fedor Ivanovich Zubkov. "Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors." Beilstein Journal of Organic Chemistry 15 (March 22, 2019): 769–79. http://dx.doi.org/10.3762/bjoc.15.73.

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A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzylamines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10−2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).

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25

Kotha, Sambasivarao, and Mirtunjay Kumar Dipak. "Design and synthesis of novel bis-annulated caged polycycles via ring-closing metathesis: pushpakenediol." Beilstein Journal of Organic Chemistry 10 (November 13, 2014): 2664–70. http://dx.doi.org/10.3762/bjoc.10.280.

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Intricate caged molecular frameworks are assembled by an atom economical process via a Diels–Alder (DA) reaction, a Claisen rearrangement, a ring-closing metathesis (RCM) and an alkenyl Grignard addition. The introduction of olefinic moieties in the pentacycloundecane (PCUD) framework at appropriate positions followed by RCM led to the formation of novel heptacyclic cage systems.

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26

Patrzałek, Michał, Aleksandra Zasada, Anna Kajetanowicz, and Karol Grela. "Tandem Olefin Metathesis/α-Ketohydroxylation Revisited." Catalysts 11, no. 6 (June 9, 2021): 719. http://dx.doi.org/10.3390/catal11060719.

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EWG-activated and polar quaternary ammonium salt-tagged ruthenium metathesis catalysts have been applied in a two-step one-pot metathesis-oxidation process leading to functionalized α-hydroxyketones (acyloins). In this assisted tandem process, the metathesis catalyst is used first to promote ring-closing metathesis (RCM) and cross-metathesis (CM) steps, then upon the action of Oxone™ converts into an oxidation catalyst able to transform the newly formed olefinic product into acyloin under mild conditions.

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27

Harit, Vimal Kant, and Namakkal G. Ramesh. "Correction: Ring closing metathesis (RCM) approach to the synthesis of conduramine B-2, ent-conduramine F-2, aminocyclopentitol and trihydroxyazepane." Organic & Biomolecular Chemistry 17, no. 26 (2019): 6506. http://dx.doi.org/10.1039/c9ob90109d.

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Correction for ‘Ring closing metathesis (RCM) approach to the synthesis of conduramine B-2, ent-conduramine F-2, aminocyclopentitol and trihydroxyazepane’ by Vimal Kant Harit et al., Org. Biomol. Chem., 2019, 17, 5951–5961.

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28

Parulekar, Sumedh, Kirankirti Muppalla, Ali Husain, and Kirpal S. Bisht. "Multifold ring closing metathesis reactions in the formation of resorcin[4]arene cavitands." RSC Advances 5, no. 32 (2015): 25477–84. http://dx.doi.org/10.1039/c5ra00760g.

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The formation of the resorcin[4]arene cavitands by the ring closing metathesis (RCM) reaction depends, to a large extent, on the conformation and the substituents on the upper and lower rim of the perallylated resorcin[4]arenes.

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29

Astruc, Didier, Abdou K. Diallo, Sylvain Gatard, Liyuan Liang, Cátia Ornelas, Victor Martinez, Denise Méry, and Jaime Ruiz. "Olefin metathesis in nano-sized systems." Beilstein Journal of Organic Chemistry 7 (January 19, 2011): 94–103. http://dx.doi.org/10.3762/bjoc.7.13.

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The interplay between olefin metathesis and dendrimers and other nano systems is addressed in this mini review mostly based on the authors’ own contributions over the last decade. Two subjects are presented and discussed: (i) The catalysis of olefin metathesis by dendritic nano-catalysts via either covalent attachment (ROMP) or, more usefully, dendrimer encapsulation – ring closing metathesis (RCM), cross metathesis (CM), enyne metathesis reactions (EYM) – for reactions in water without a co-solvent and (ii) construction and functionalization of dendrimers by CM reactions.

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30

Rodríguez, A. M., P. Prieto, A. de la Hoz, A. Díaz-Ortiz, and J. I. García. "The issue of ‘molecular radiators’ in microwave-assisted reactions. Computational calculations on ring closing metathesis (RCM)." Org. Biomol. Chem. 12, no. 15 (2014): 2436–45. http://dx.doi.org/10.1039/c3ob42536c.

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31

Bolm, Carsten, and Hélène Villar. "Ring-Closing Metathesis (RCM) for the Synthesis of Cyclic Sulfoximines." Synthesis, no. 9 (2005): 1421–24. http://dx.doi.org/10.1055/s-2005-865312.

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32

Yadav, Jhillu S., Chitteti Divya Vani, Mule Chowdeswari, K. Ananthalakshmi, N. Bhasker, and Basi V. Subba Reddy. "First Stereoselective Total Synthesis of (3S,7R)-De-O-methylbotryosphaeriodiplodin." Natural Product Communications 14, no. 1 (January 2019): 1934578X1901400. http://dx.doi.org/10.1177/1934578x1901400136.

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A simple and highly efficient first stereoselective total synthesis of a benzofused macrocyclic lactone, ( 3S,7R)-de- O-methylbotryosphaeriodiplodin has been accomplished utilizing Jacobson's kinetic resolution, Marouka asymmetric allylation, Stille coupling, and ring-closing metathesis (RCM) reactions as key steps.

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33

Kotha, Sambasivarao, and Sunil Pulletikurti. "Synthesis of propellanes containing a bicyclo[2.2.2]octene unitviathe Diels–Alder reaction and ring-closing metathesis as key steps." RSC Advances 8, no. 27 (2018): 14906–15. http://dx.doi.org/10.1039/c8ra02687d.

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A simple and convenient method to synthesize propellane derivatives containing a bicyclo[2.2.2]octene unit which are structurally similar to 11β-HSD1 inhibitors by sequential usage of the Diels–Alder reaction, C-allylation and ring-closing metathesis (RCM) is reported.

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34

Babu, K., Arramshetti Venkanna, Borra Poornima, Bandi Siva, and B. Babu. "Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core." Synlett 29, no. 07 (February 19, 2018): 908–11. http://dx.doi.org/10.1055/s-0036-1591539.

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A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

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35

Lecourt, C., S. Dhambri, L. Allievi, Y. Sanogo, N. Zeghbib, R. Ben Othman, M. I. Lannou, G. Sorin, and J. Ardisson. "Natural products and ring-closing metathesis: synthesis of sterically congested olefins." Natural Product Reports 35, no. 1 (2018): 105–24. http://dx.doi.org/10.1039/c7np00048k.

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36

Burt, Michael B., Angela K. Crane, Ning Su, Nicole Rice, and Raymond A. Poirier. "Ring-chain equilibria of R-but-3-enoate esters — A quantum mechanical study of direct and indirect ring-closing reactions." Canadian Journal of Chemistry 88, no. 11 (November 2010): 1094–103. http://dx.doi.org/10.1139/v10-074.

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Macrocyclic structures can be synthesized through two simultaneous olefin metathesis reactions: either directly through ring-closing metathesis (RCM) or indirectly through an intermediate formed by acyclic diene metathesis (ADMET). The proclivity of a homologous series of 16 R-but-3-enoate esters to form lactones through one of these two processes is studied at the HF/6–31G(d), B3LYP/6–31G(d), and MP2(full)/6–31G(d) levels of theory. Computed Gibbs free energies are used to determine ΔGRCM, ΔGADMET, and ΔΔG (ΔGRCM – ΔGADMET). ΔΔG is evaluated to compare the relative favourability of the RCM and ADMET reactions for the various R-but-3-enoate esters, where each system is differentiated by the number of methylene groups (n) added to the ester chain. When n = 0, 1, 10, or 13, cyclic lactone formation by direct RCM is predicted to be thermodynamically favoured, and the indirect synthesis is preferred for all other heterocyclic structures. The same trend holds between 298.15 and 333.15 K, therefore, the gas-phase model is a reasonable approximation of the experimental reaction conditions. The theoretical model is sufficient for smaller systems, but molecules larger than the n = 6 case do not follow experimental results for similar saturated structures. Hence, the assumptions pertaining to straight-chain and cis-ring conformations need to be re-evaluated. In particular, chain flexibility should be further examined.

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37

Ramachandran, P. Veeraraghavan, M. Venkat Ram Reddy, and Herbert C. Brown. "Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules." Pure and Applied Chemistry 75, no. 9 (January 1, 2003): 1263–75. http://dx.doi.org/10.1351/pac200375091263.

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The development of asymmetric synthesis during the past two decades aided organic chemists considerably in the synthesis of complex natural products. Organoborane chemistry continues to play an important role in asymmetric synthesis. One of the important reactions that has become very common in the arsenal of synthetic chemists is allylboration and related reactions. Another important reaction that has recently attained enormous importance in organic chemistry is the ring-closing metathesis (RCM) reaction. Indeed, a combination of allylboration and RCM reactions provides an excellent route to cyclic ethers, lactones, lactams, etc. Herein, we describe a sequential asymmetric allylboration and RCM reaction protocol that has been utilized for the synthesis of several alpha-pyrone-containing natural products,particularly biologically active molecules.

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38

Wakamatsu, Hideaki, Yuichi Yoshimura, Yoshimi Sasaki, Masatoshi Kawahata, and Kentaro Yamaguchi. "Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides." Synthesis 50, no. 17 (May 30, 2018): 3467–86. http://dx.doi.org/10.1055/s-0037-1609857.

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Ring-closing metathesis (RCM) of ynamides, having alkene substituents of various lengths on the side chain, was demonstrated using the second-generation Grubbs catalyst. When the reaction of ene-ynamides was carried out in the presence of 5 mol% of the catalyst, RCM proceeded smoothly to give quinoline or isoquinoline derivatives having a dienamide unit in good yields. Furthermore, RCM of ene-ynamides, having one more carbon on the side chain, proceeded smoothly to provide seven-membered heterocycles having a dienamide component. Similarly, eight-membered heterocycles, diazocine and benzodiazocine, were also synthesized by RCM of ene-ynamides in good yields.

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39

Kotha, Sambasivarao, and Sunil Pulletikurti. "A Metathetic Approach to [5/5/6] Aza-Tricyclic Core of Dendrobine, Kopsanone, and Lycopalhine A Type of Alkaloids." Synthesis 51, no. 21 (September 13, 2019): 3981–88. http://dx.doi.org/10.1055/s-0039-1690620.

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A concise synthetic approach to [5/5/6] tricyclic pyrrolidine core of dendrobine is reported. This methodology relies on the construction of β-hydroxylactams by NaBH4-I2 reduction followed by reaction of allylsilane with the aid of Lewis acid to generate alkenyl lactams in good yields. Further, ring-opening metathesis (ROM) followed by ring-closing metathesis (RCM) were used to assemble the [5/5/6] aza-tricyclic skeleton of dendrobine. This short synthetic route has been expanded to assemble tricyclic [5/5/8] system with pentenylboronic acid.

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40

Kotha, Sambasivarao, Vital Seema, Deepak Deodhar, and Mobin Shaikh. "Crystal structures of 3,6-diallyltetracyclo[6.3.0.04,11.05,9]undeca-2,7-dione and 1,7-diallylpentacyclo[5.4.0.02,6. 03,10.05,9]undecane-8,11-dione: allylated caged compounds." Acta Crystallographica Section E Structure Reports Online 70, no. 11 (October 24, 2014): 410–14. http://dx.doi.org/10.1107/s1600536814023149.

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The title compounds, C17H20O2(1) and C17H18O2(2), are allylated caged compounds. In (1), the carbon atoms bearing the allyl groups are far apart [2.9417 (17) Å], hence the expected ring-closing metathesis (RCM) protocol failed to give a ring-closing product. When these carbon atoms are connected by a C—C bond as in (2), the distance between them is much smaller [1.611 (3) Å] and consequently the RCM process was successful. The caged carbon skeleton of (1) can be described as a fusion of four five-membered rings and one six-membered ring. All four five-membered rings exhibit envelope conformations. The structure of compound (2) consists of four five-membered rings, of which two are cyclopentanone rings bonded at the 2, 4 and 5 positions and linked at the 3-carbons by a methylene bridge. It also consists of one four-membered and two six-membered rings. All four five-membered rings adopt envelope conformations. In the crystal of (1), molecules are linkedviaC—H...O hydrogen bonds, forming sheets lying parallel to (010). In the crystal of (2), molecules are linkedviaC—H...O hydrogen bonds forming chains along [100].

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41

Adler, Pauline, Antoine Fadel, Joëlle Prunet, and Nicolas Rabasso. "From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis." Organic & Biomolecular Chemistry 15, no. 2 (2017): 387–95. http://dx.doi.org/10.1039/c6ob02548j.

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42

Arisawa, Mitsuhiro, Atsushi Nishida, and Chumpol Theeraladanon. "Preparation of N-Sulfonyl-2-quinolinone Using Ring-closing Metathesis (RCM)." HETEROCYCLES 66, no. 1 (2005): 683. http://dx.doi.org/10.3987/com-05-s(k)72.

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43

Yadav, J. S., K. Anantha Lakshmi, N. Mallikarjuna Reddy, Attaluri R. Prasad, and Basi V. Subba Reddy. "Stereoselective total synthesis of decarestrictine-J via Ring Closing Metathesis (RCM)." Tetrahedron 66, no. 1 (January 2010): 334–38. http://dx.doi.org/10.1016/j.tet.2009.10.100.

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44

Banerjee, Shyamapada, Abhijit Nayek, Saikat Sinha, Tanurima Bhaumik, and Subrata Ghosh. "Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes." Journal of Molecular Catalysis A: Chemical 254, no. 1-2 (July 2006): 85–92. http://dx.doi.org/10.1016/j.molcata.2006.03.023.

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45

Arisawa, Mitsuhiro, Hiroaki Kaneko, Atsushi Nishida, and Masako Nakagawa. "Stereoselectivity in ring-closing olefin metathesis (RCM) of tethered dihexenoyl derivatives." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (March 1, 2002): 959–64. http://dx.doi.org/10.1039/b111122c.

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46

Gersbach, Philipp, Andrea Jantsch, Fabian Feyen, Nicole Scherr, Jean-Pierre Dangy, Gerd Pluschke, and Karl-Heinz Altmann. "A Ring-Closing Metathesis (RCM)-Based Approach to Mycolactones A/B." Chemistry - A European Journal 17, no. 46 (October 4, 2011): 13017–31. http://dx.doi.org/10.1002/chem.201101799.

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47

Arisawa, Mitsuhiro, Chiaki Kato, Hiroaki Kaneko, Atsushi Nishida, and Masako Nakagawa. "ChemInform Abstract: Concise Synthesis of Azacycloundecenes Using Ring-Closing Metathesis (RCM)." ChemInform 31, no. 41 (October 10, 2000): no. http://dx.doi.org/10.1002/chin.200041177.

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48

Vázquez, Alfredo, and Maricela Morales-Chamorro. "A Facile Synthesis of N-Boc-azocan-5-one." Synthesis 51, no. 04 (October 10, 2018): 842–47. http://dx.doi.org/10.1055/s-0037-1611018.

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The azacycloalkane 1-azocan-5-one is embedded in the structure of several products of natural origin displaying a variety of bioactivities. Two convenient and straightforward routes were developed to synthesize N-Boc-azocan-5-one from readily available raw materials featuring a ring-closing metathesis (RCM) reaction as the key step.

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49

Ghanty, Supriya, P. Rasvan Khan, and B. V. Subba Reddy. "Stereoselective Total Syntheses of (3R,5R)-Sonnerlactone and (3R,5S)-Sonnerlactone." Natural Product Communications 12, no. 9 (September 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200925.

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A highly convergent and concise total syntheses of (3 R,5 R)-Sonnerlactone and (3 R,5 S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.

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50

Tracz, Andrzej, Mateusz Matczak, Katarzyna Urbaniak, and Krzysztof Skowerski. "Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions." Beilstein Journal of Organic Chemistry 11 (October 6, 2015): 1823–32. http://dx.doi.org/10.3762/bjoc.11.198.

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Iodide-containing nitro-Grela-type catalysts have been synthesized and applied to ring closing metathesis (RCM) and cross metathesis (CM) reactions. These new catalysts have exhibited improved efficiency in the transformation of sterically, non-demanding alkenes. Additional steric hindrance in the vicinity of ruthenium related to the presence of iodides ensures enhanced catalyst stability. The benefits are most apparent under challenging conditions, such as very low reaction concentrations, protic solvents or with the occurrence of impurities.

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