Relevant bibliographies by topics / Transannular cyclizations

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  2. Dissertations / Theses
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Academic literature on the topic 'Transannular cyclizations'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Transannular cyclizations"

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Jahn, Ullrich, and Dennis P. Curran. "Towards a tandem-radical macrocyclization-transannular cyclization approach to steroids: Transannular cyclizations of a macrocyclic core." Tetrahedron Letters 36, no. 49 (December 1995): 8921–24. http://dx.doi.org/10.1016/0040-4039(95)01918-8.

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JAHN, U., and D. P. CURRAN. "ChemInform Abstract: Towards a Tandem-Radical Macrocyclization-Transannular Cyclization Approach to Steroids: Transannular Cyclizations of a Macrocyclic Core." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613100.

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Yamato, Takehiko, Koji Fujita, Keigo Futatsuki, and Hirohisa Tsuzuki. "Medium-sized cyclophanes. Part 53.1 Synthesis and conformational studies, and photoinduced cyclization of syn-[n.2]metacyclophanenes." Canadian Journal of Chemistry 78, no. 8 (August 1, 2000): 1089–99. http://dx.doi.org/10.1139/v00-110.

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A series of [n.2]metacyclophanenes (3) and (6) were prepared in good yields by a McMurry cyclization of 1,n-bis(3-acetyl-4-methoxyphenyl)alkanes (2) and 1,3-bis(3-formyl-4-methoxyphenyl)propane (5), respectively. Compounds 3b, 3c exist in the syn-conformation due to the steric repulsion between the methyl groups at the ethano bridge and the methoxy groups at the aromatic rings while compound 6 prefers the anti-conformation typical of [3.2]metacyclophanes. The assignment of syn-conformations has been confirmed by 1H NMR analyses and X-ray diffraction studies. Photoinduced transannular cyclization of [n.2]metacyclophanenes (3) and (6) in the presence of iodine as an oxidant afforded phenanthrene-anellated polycyclic aromatic hydrocarbons. Apparently, the rate of the photocyclization of anti-6 was found to be much faster than that of syn-3b and almost completed within 1 h. Thus, the different reactivities for the irradiation of syn- and anti-conformer were observed. The reason for the present preference for the formation of trans-dihydrophenanthrene rather than cis-dihydrophenanthrene as the intermediate might be attributable to the more stable chair form transition state than boat one and the conformational fixation to the chair form in the ground and transition state is possible in the anti-conformer.Key words: cyclophanes, strained molecule, McMurry reaction, C—C coupling, conformation analysis, cyclizations, photolysis, transannular reactions, transition states.
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Kende, Andrew S., Clara E. Mota Nelson, and Sébastien Fuchs. "Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes." Tetrahedron Letters 46, no. 47 (November 2005): 8149–52. http://dx.doi.org/10.1016/j.tetlet.2005.09.125.

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Rychlet Elliott, Maryse, Anne-Lise Dhimane, and Max Malacria. "Biomimetic Diastereoselective Total Synthesis ofepi-Illudolviaa Transannular Radical Cyclizations Strategy." Journal of the American Chemical Society 119, no. 14 (April 1997): 3427–28. http://dx.doi.org/10.1021/ja970139i.

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Han, Chong, Sathish Rangarajan, Alicia C. Voukides, Aaron B. Beeler, Richard Johnson, and John A. Porco. "Reaction Discovery Employing Macrocycles: Transannular Cyclizations of Macrocyclic Bis-lactams." Organic Letters 11, no. 2 (January 15, 2009): 413–16. http://dx.doi.org/10.1021/ol802729f.

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Williams, David R., and Paul J. Coleman. "Studies on the dolabellanes: Stereoselective transannular cyclizations of dolabelladiene macrocycles." Tetrahedron Letters 36, no. 1 (January 1995): 39–42. http://dx.doi.org/10.1016/0040-4039(94)02164-7.

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Curran, Dennis P., and Wang Shen. "Tandem transannular radical cyclizations. Total syntheses of (±)-modhephene and (±)-epi-modhephene." Tetrahedron 49, no. 4 (January 1993): 755–70. http://dx.doi.org/10.1016/s0040-4020(01)80321-5.

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HANDA, S., and G. PATTENDEN. "ChemInform Abstract: Free Radical-Mediated Macrocyclizations and Transannular Cyclizations in Synthesis." ChemInform 28, no. 37 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199737382.

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Doi, Takayuki, and Takashi Takahashi. "Syntheses and transannular cyclizations of neocarzinostatin-chromophore and esperamicin-calichemicin analogs." Journal of Organic Chemistry 56, no. 11 (May 1991): 3465–67. http://dx.doi.org/10.1021/jo00011a002.

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Dissertations / Theses on the topic "Transannular cyclizations"

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Atmuri, Nagavenkata. "Azabicycloalkanone synthesis by transannular cyclization." Thèse, 2014. http://hdl.handle.net/1866/12518.

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Une stratégie de synthèse efficace de différents composés de type azabicyclo[X.Y.0]alkanone fonctionnalisés a été développée. La stratégie synthétique implique la préparation de dipeptides par couplage avec des motifs vinyl-, allyl-, homoallyl- et homohomoallylglycine suivi d’une réaction de fermeture de cycle par métathèse permettant d’obtenir des lactames macrocycliques de 8, 9 et 10 membres, qui subissent une iodolactamisation transannulaire menant à l’obtention de mimes peptidiques bicycliques portant un groupement iode. Des couplages croisés catalysés par des métaux de transition ont été développés pour la synthèse d’acides aminés ω-insaturés énantiomériquement purs à partir de l’iodoanaline. L’étude du mécanisme suggère que l’iodure subit une attaque du coté le moins stériquement encombré de la lactame macrocyclique insaturée pour mener à l’obtention d’un intermédiaire iodonium. La cyclisation se produit ensuite par une route minimisant les interactions diaxiales et la tension allylique. L’iodolactamisation des différentes lactames macrocycliques insaturées a mené à l’obtention regio- et diastéréosélective d’acides aminés 5,5- et 6,6-iodobicycicliques. De plus, une imidate azabicyclo[4.3.1]alkane pontée de type anti-Bredt fut synthétisée à partir d’une lactame macrocyclique insaturé à neuf membres. Les analyses cristallographiques et spectroscopiques des macrocycles à 8, 9 et 10 membres, du composé iodobicyclique 5,5 ainsi que de l’imidate pontée, montrent bien le potentiel de ces dipeptides rigidifiés de servir en tant que mimes des résidus centraux de tours β de type I, II’, II et VI.
An efficient strategy has been developed for the synthesis of different functionalized azabicyclo[X.Y.0]alkanone amino acids. The synthetic sequence features preparation of dipeptides by coupling respectively vinyl-, allyl-, homoallyl- and homohomoallylglycine building blocks, followed by ring closing metathesis to produced 8-, 9-, and 10-member unsaturated macrocyclic lactams, and transannular iodolactamization to make the bicyclic dipeptide surrogates bearing iodine on the lactam ring. Transition metal cross-coupling methods were developed to make enantiomerically pure ω-unsaturated amino acid building blocks from iodoalanine. Mechanistic considerations suggest that attack of iodine from the least hindered face of the unsaturated macrocyclic lactam provides an iodonium intermediate and cyclization occurs by a route that minimizes allylic strain and diaxial interactions. Iodolactamization of the unsaturated macrocyclic lactams gave regio- and diastereoselectively fused 5,5- and 6,6-iodo-bicylic amino acids. Moreover, an anti-Bredt bridgehead imidate azabicyclo[4.3.1]alkane was synthesized from a 9-membered unsaturated macrocyclic lactam precursor. X-ray crystallographic and spectroscopic analyses of the 8-, 9-, and 10-member macrocycles, as well as the 5,5-bicycle and bridgehead imidate demonstrate the potential of these constrained dipeptides to mimic the central residues of ideal type I, II’, II and VI β-turn geometry.
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Condroski, Kevin Ronald. "Synthesis of (±)-7,8-Epoxy-4-basmen-6-one by a Transannular Cyclization Strategy." Thesis, 1994. https://thesis.library.caltech.edu/7646/1/Condroski_kr_1994.pdf.

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The first synthesis of the cembranoid natural product (±)-7,8-epoxy-4-basmen-6-one (1) is described. Key steps of the synthetic route include the cationic cyclization of the acid chloride from 15 to provide the macrocycle 16, and the photochemical transannular radical cyclization of the ester 41 to form the tricyclic product 50. Product 50 was transformed into 1 in ten steps. Transition-state molecular modeling studies were found to provide accurate predictions of the structural and stereochemical outcomes of cyclization reactions explored experimentally in the development of the synthetic route to 1. These investigations should prove valuable in the development of transannular cyclization as a strategy for synthetic simplification.
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Atmuri, Nagavenkata. "Design, synthesis and biomedical applications of Azabicycloalkanone Amino Acid Peptidomimetics." Thèse, 2019. http://hdl.handle.net/1866/22629.

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Book chapters on the topic "Transannular cyclizations"

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Harrowven, David C., and Gerald Pattenden. "Transannular Electrophilic Cyclizations." In Comprehensive Organic Synthesis, 379–411. Elsevier, 1991. http://dx.doi.org/10.1016/b978-0-08-052349-1.00067-6.

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Dao, T. T. H., T. Marmin, and Y. L. Dory. "3.06 Transannular Electrophilic Cyclizations." In Comprehensive Organic Synthesis II, 293–336. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-08-097742-3.00310-4.

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Avendaño, C., and J. C. Menéndez. "Transannular Cyclizations of [2]Metacyclophanes with -Bromosuccinimide." In Quinones and Heteroatom Analogues, 1. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-028-00746.

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"1.5.5: 1.5.5.4. Transannular Carbenium Ion Olefin Cyclizations." In Stereoselective Synthesis, edited by Günter Helmchen, Reinhard W. Hoffmann, Johann Mulzer, and Ernst Schaumann. Stuttgart: Georg Thieme Verlag, 1995. http://dx.doi.org/10.1055/b-0035-114235.

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Diederich, F., R. R. Tykwinski, and M. B. Nielsen. "Transannular Cyclization." In Polyynes, Arynes, Enynes, and Alkynes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-043-00103.

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Taber, Douglass F. "Tethered Diels-Alder Cycloaddition: (±)-Neovibsanin B (Imagawa, Nishizawa), Valerenic Acid (Mulzer), (-)-Himandrine (Movassaghi), (±)-Pallavicinolide A (Wong), (+)-Phomopsidin (Nakada)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0077.

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It has generally been observed that prospective intramolecular Diels-Alder cycloadditions that would form a γ-lactone are reluctant to proceed. In the course of a synthesis of (±)-neovibsanin B 4, Hiroshi Imagawa and Mugio Nishizawa of Tokushima Bunri University reversed (Organic Lett. 2009, 11, 1253) the usual connectivity and found that the dienyl ester 1 could be induced to cyclize to 3. The solvent 2 improved both the yield and the diastereoselectivity of the cycloaddition. It was not surprising that Johann Mulzer of the University of Vienna could see (Organic Lett. 2009, 11, 1151) no evidence of cyclization on heating the acrylate 5. In contrast, following the lead of Barriault, they found that MgBr2 -tethered cycloaddition of methyl acrylate 7 with the alcohol 6 proceeded smoothly, to give 8, which they carried on to valerenic acid 9. Intramolecular Diels-Alder reactions to form 6,6-systems are often facile. Mohammad Movassaghi of MIT, en route to (-)-himandrine 12, showed (J. Am. Chem. Soc. 2009, 131, 9648) that the tetraene 10 cyclized to 11 at 95°C with 5:1 dr. In this case the solvent was the more typical acetonitrile with 10% diethyl aniline. The intramolecular Diels-Alder reaction is concerted but nonsynchronous (Tetrahedron Lett. 1981, 22, 5141), with β-bond formation preceding α-bond formation. This contributes to the reluctance of 8 to cyclize. In contrast, Henry N. C. Wong of the Chinese University of Hong Kong observed (Angewandte Chem. Int. Ed. 2009, 48, 2351) that the tetraene 13, which is polarity matched, cyclized to 14 spontaneously as soon as it was formed. Functional group conversion completed the synthesis of (±)-pallavicinolide A 15. The transannular Diels-Alder (TADA) reaction can proceed with high diastereocontrol, but the factors directing these cyclizations are not completely understood. In the course of a synthesis of (+)-phomopsidin 18, Masahisa Nakada of Waseda University found (Tetrahedron 2009, 65, 888) that 16 led to 17 with 16:1 dr. In contrast, the triene epimeric to 16 at the silyloxy group cyclized with only 2:1 dr.
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Taber, Douglass. "The Roush Synthesis of ( + )-Superstolide A." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0093.

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( + )-Superstolide A 3, isolated from the New Caledonian sponge Neosiphonia superstes, shows interesting cytotoxicity against malignant cell lines at ~ 4 ng/mL concentration. The key transformation in the synthesis of 3 described (J. Am. Chem. Soc. 2008, 130, 2722) by William R. Roush of Scripps Florida was the transannular Diels-Alder cyclization of 2, which established, in one step with high diastereocontrol, both the cis decalin and the macrolactone of 3. The octaene 1 was assembled from four stereodefined fragments. The first, the linchpin 6, was prepared from the stannyl aldehyde 4. Homologation gave the enyne 5, which on hydroboration and oxidation gave 6. Earlier, Professor Roush had optimized the crotylation of the protected alaninal 7. In this case, the Brown reagent 8 delivered the desired Felkin product 9. Protection followed by ozonolysis gave the aldehyde 10. Crotylation with the Roush-developed tartrate 11 then gave the alkene 12, setting the stage for conversion to the iodide 13. Coupling of 13 with 6 completed the preparation of 14. The third component of (+)-superstolide A 3, the phosphonium salt 21, was assembled by Brown allylation of the aldehyde 15, to give 17. Protecting group interchange followed by ozonolysis delivered 18, which via Still-Gennari homologation was carried on to 21. Condensation with the fourth component, the aldehyde 22 , and esterification with 14 then gave 1. Under high dilution Suzuki conditions 1 was converted to 2. Storage in CDCl3 for five days, or brief warming, cyclized 2 to a single diastereomer of the transannular Diels-Alder product, that was carried on to (+)-superstolide A 3. While acyclic trienes comparable to 2 could be induced to cyclize, the transannular Diels-Alder reaction proceeded with much higher diastereocontrol.
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Taber, Douglass. "Total Synthesis by Alkene Metathesis: Amphidinolide X (Urpí/Vilarrasa), Dactylolide (Jennings), Cytotrienin A (Hayashi), Lepadin B (Charette), Blumiolide C (Altmann)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0031.

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To assemble the framework of the cytotoxic macrolide Amphidinolide X 3, Fèlix Urpí and Jaume Vilarrasa of the Universitat de Barcelona devised (Organic Lett. 2008, 10, 5191) the ring-closing metathesis of the alkenyl silane 1. No Ru catalyst was effective, but the Schrock Mo catalyst worked well. In the course of a synthesis of (-)-Dactylolide 6, Michael P. Jennings of the University of Alabama offered (J. Org. Chem. 2008, 73, 5965) a timely reminder of the particular reactivity of allylic alcohols in ring-closing metathesis. The cyclization of 4 to 5 proceeded smoothly, but attempted ring closing of the corresponding bis silyl ether failed. Polyenes such as ( + )-Cytotrienin A 8 are notoriously unstable. It is remarkable that Yujiro Hayashi of the Tokyo University of Science could (Angew. Chem. Int. Ed. 2008, 47, 6657) assemble the triene of 8 by the ring-closing metathesis of the highly functionalized precursor 7. Bicyclo [2.2.2] structures such as 9 are readily available by the addition of, in this case, methyl acrylate to an enantiomerically-pure 2-methylated dihydropyridine. André B. Charette of the Université de Montréal found (J. Am. Chem. Soc. 2008, 130, 13873) that 9 responded well to ring-opening/ring-closing metathesis, to give the octahydroquinoline 10. Functional group manipulation converted 10 into the Clavelina alkaloid ( + )-Lepadin B 11. The construction of trisubstituted alkenes by ring-closing metathesis can be difficult, and medium rings with their transannular strain are notoriously challenging to form. Nevertheless, Karl-Heinz Altmann of the ETH Zürich was able (Angew. Chem. Int. Ed. 2008, 47, 10081), using the H2 catalyst, to cyclize 12 to cyclononene 13, the precursor to the Xenia lactone ( + )-Blumiolide C 14. It is noteworthy that these fi ve syntheses used four different metathesis catalysts in the key alkene forming step. For the cyclization of 7, the use of the Grubbs first generation catalyst G1, that couples terminal alkenes but tends not to interact with internal alkenes, was probably critical to success.
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