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Journal articles on the topic 'Diels-Alder reaction. Biosynthesis. Natural products'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Cottet, Kévin, Maria Kolympadi, Dean Markovic, and Marie-Christine Lallemand. "Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction." Current Organic Chemistry 20, no. 22 (2016): 2421–42. http://dx.doi.org/10.2174/1385272820666160331234709.

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2

Watanabe, Kenji. "Discovery and investigation of natural Diels–Alderases." Journal of Natural Medicines 75, no. 3 (2021): 434–47. http://dx.doi.org/10.1007/s11418-021-01502-4.

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AbstractIt has been proposed that biosyntheses of many natural products involve pericyclic reactions, including Diels–Alder (DA) reaction. However, only a small set of enzymes have been proposed to catalyze pericyclic reactions. Most surprisingly, there has been no formal identification of natural enzymes that can be defined to catalyze DA reactions (DAases), despite the wide application of the reaction in chemical syntheses of complex organic compounds. However, recent studies began to accumulate a growing body of evidence that supports the notion that enzymes that formally catalyze DA reacti

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3

Oikawa, Hideaki, and Tetsuo Tokiwano. "Enzymatic catalysis of the Diels–Alder reaction in the biosynthesis of natural products." Nat. Prod. Rep. 21, no. 3 (2004): 321–52. http://dx.doi.org/10.1039/b305068h.

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4

Oikawa, Hideaki, Yuichi Suzuki, Kinya Katayama, Akira Naya, Chiaki Sakano, and Akitami Ichihara. "Involvement of Diels–Alder reactions in the biosynthesis of secondary natural products: the late stage of the biosynthesis of the phytotoxins solanapyrones." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (1999): 1225. http://dx.doi.org/10.1039/a807704e.

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5

Oikawa, Hideaki, Yuichi Suzuki, Kinya Katayama, Akira Naya, Chiaki Sakano, and Akitami Ichihara. "ChemInform Abstract: Involvement of Diels-Alder Reactions in the Biosynthesis of Secondary Natural Products: The Late Stage of the Biosynthesis of the Phytotoxins Solanapyrones." ChemInform 30, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199938216.

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6

Lam, Hiu C., Quang D. Phan, Christopher J. Sumby, and Jonathan H. George. "Biomimetic Synthesis of Hyperjapones F-I." Australian Journal of Chemistry 71, no. 9 (2018): 649. http://dx.doi.org/10.1071/ch18141.

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Hyperjapones F–I are tetracyclic meroterpenoids recently isolated from Hypericum japonicum. All four of these natural products have been synthesised using oxidative, intermolecular hetero-Diels–Alder reactions to couple their common biosynthetic precursor, norflavesone, to the appropriate monoterpene building blocks: sabinene, β-pinene, and α-pinene. The synthesis of enantiomerically pure hyperjapones H and I and comparison of their optical rotations to those of the natural samples indicated that these meroterpenoids are probably biosynthesised as either racemic or scalemic mixtures.

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7

Cao, Min-Hui, Nicholas J. Green, and Sheng-Zhen Xu. "Application of the aza-Diels–Alder reaction in the synthesis of natural products." Organic & Biomolecular Chemistry 15, no. 15 (2017): 3105–29. http://dx.doi.org/10.1039/c6ob02761j.

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8

LIU, Z. Y., X. J. CHU, L. HE, Y. N. XIE, and L. Y. ZHAO. "ChemInform Abstract: Natural Products Synthesis by Retro-Diels-Alder Reaction." ChemInform 28, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199725278.

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9

Nasir, Shah Bakhtiar, Noorsaadah Abd Rahman, and Chin Fei Chee. "Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review." Current Organic Synthesis 15, no. 2 (2018): 221–29. http://dx.doi.org/10.2174/1570179414666170821120234.

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Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples.

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10

Lee, Chi-Sing, Guangyan Du, Gaopeng Wang, et al. "Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions." Synlett 28, no. 12 (2017): 1394–406. http://dx.doi.org/10.1055/s-0036-1588777.

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The σ/π-binding properties of a series of Lewis acids was studied using DFT calculations. The results led to the identification of Zn(II)/In(III) as a suitable dual-mode Lewis acid for use in promoting cascade cyclization reactions. Based on this finding, we developed three new types of dual-mode Lewis acid induced cascade cyclization reactions and have demonstrated the utilities of each process in natural product synthesis.1 Introduction2 Dual-Mode Lewis Acids3 Prins/Conia-Ene Cascade Reaction and its Applications4 Diels–Alder/Carbocyclization Cascade Reaction and Applications4.1 First Genera

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11

Heravi, Majid M., and Vaezeh Fathi Vavsari. "Recent applications of intramolecular Diels–Alder reaction in total synthesis of natural products." RSC Advances 5, no. 63 (2015): 50890–912. http://dx.doi.org/10.1039/c5ra08306k.

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12

Feng, Minghao, and Xuefeng Jiang. "Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products." Chem. Commun. 50, no. 68 (2014): 9690–92. http://dx.doi.org/10.1039/c4cc04148h.

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13

Liu, Hsing-Jang, Wen-Lung Yeh, and Eric N. C. Browne. "Activated cycloheptenone dienophiles. A versatile approach to 6,7-fused ring targets." Canadian Journal of Chemistry 73, no. 7 (1995): 1135–47. http://dx.doi.org/10.1139/v95-140.

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Several 2-carbalkoxy-2-cyclohepten-1-ones were prepared and their Diels–Alder characteristics examined in order to develop a facile general approach to the synthesis of cycloheptane ring-containing polycyclic natural products. Substitution pattern on the seven-membered ring was found to greatly affect the Diels–Alder behavior. In addition, some extraordinary facial stereoselectivity was observed. Keywords: Diels–Alder reaction, 2-carbalkoxy-2-cyclohepten-1-ones, 6,7-fused ring system.

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14

Heravi, Majid M., Tahereh Ahmadi, Mahdieh Ghavidel, Bahareh Heidari, and Hoda Hamidi. "Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products." RSC Advances 5, no. 123 (2015): 101999–2075. http://dx.doi.org/10.1039/c5ra17488k.

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15

Williard, Paul G., and Stephen E. De Laszlo. "Total synthesis of halogenated monoterpene marine natural products via the Diels-Alder reaction." Journal of Organic Chemistry 50, no. 20 (1985): 3738–49. http://dx.doi.org/10.1021/jo00220a013.

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16

Ohba, Masashi. "ChemInform Abstract: Synthesis of Natural Products via Intramolecular Oxazole-Olefin Diels-Alder Reaction." ChemInform 42, no. 51 (2011): no. http://dx.doi.org/10.1002/chin.201151221.

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17

Tietze, L. F., and N. Rackelmann. "Domino reactions in the synthesis of heterocyclic natural products and analogs." Pure and Applied Chemistry 76, no. 11 (2004): 1967–83. http://dx.doi.org/10.1351/pac200476111967.

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Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way. A very powerful domino process is the domino Knoevenagel–hetero-Diels–Alder reaction, in which an aldehyde or an beta-ketoester is condensed with a 1,3-dicarbonyl compound or a heteroanalog to give a 1-oxa-1,3-butadiene, which can undergo an inter-

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18

Miyashita, Masaaki. "Recent progress in the synthesis of bioactive polycyclic natural products." Pure and Applied Chemistry 79, no. 4 (2007): 651–65. http://dx.doi.org/10.1351/pac200779040651.

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The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties as well as their unique chemical structures with stereochemical complexity. Namely, norzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug, whereas zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoant

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19

Carosso, Serena, and Marvin J. Miller. "Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products." Org. Biomol. Chem. 12, no. 38 (2014): 7445–68. http://dx.doi.org/10.1039/c4ob01033g.

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This review describes the use of nitroso Diels–Alder reactions for the functionalization of complex diene-containing natural products in order to generate libraries of compounds with potential biological activity.

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20

Kramer, Carsten S., and Stefan Bräse. "Thiourea-catalyzed Diels–Alder reaction of a naphthoquinone monoketal dienophile." Beilstein Journal of Organic Chemistry 9 (July 12, 2013): 1414–18. http://dx.doi.org/10.3762/bjoc.9.158.

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A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels–Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective synthesis of the exo-product 2a in up to 63% yield. In this reaction a new quaternary center was built. The so formed cycloaddition product 2a represents the ABC tricycle of beticolin 0 (1) and is also

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21

Goodrich, P., H. Q. Nimal Gunaratne, L. Hall, et al. "Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction." Dalton Transactions 46, no. 5 (2017): 1704–13. http://dx.doi.org/10.1039/c6dt04572c.

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A bis-oxazoline ligand has been complexed using Cu(ii) and Zn(ii) trifluoromethanesulfonate and a range of chiral ionic liquid (CIL) additives based on natural products were used as a co-catalyst for a Diels–Alder reaction.

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22

Shiina, Junichi, and Shigeru Nishiyama. "Intramolecular Diels–Alder reaction leading to tricyclic derivatives as intermediates of natural products synthesis." Tetrahedron 59, no. 32 (2003): 6039–44. http://dx.doi.org/10.1016/s0040-4020(03)01013-5.

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23

Ran, Hongyu, and Gangliang Huang. "The Diels-Alder Reaction and its Applications in the Total Synthesis of Natural Products." Current Organic Synthesis 13, no. 6 (2016): 847–60. http://dx.doi.org/10.2174/1570179413666160624111111.

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24

Wan, ChunYun, Jun Deng, Hua Liu, Ming Bian, and Ang Li. "Recent advances of intermolecular Diels-Alder reaction in bio-inspired synthesis of natural products." Science China Chemistry 57, no. 7 (2014): 926–29. http://dx.doi.org/10.1007/s11426-014-5144-5.

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25

Xu, Yao-Chang, Andrew L. Roughton, Raymond Plante, Solo Goldstein, and Pierre Deslongchamps. "Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part I. Transannular Diels–Alder reactions of 14-membered macrocycles containing trans-dienophiles." Canadian Journal of Chemistry 71, no. 8 (1993): 1152–68. http://dx.doi.org/10.1139/v93-152.

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Transannular Diels–Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures 1a, 1b, and 1c having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular displacement of an allylic halide by the anion of an appropriately located dimethyl malonate unit. The transannular Diels–Alder reaction performed on 1a led to a mixture

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26

Chen, Ling, and Pierre Deslongchamps. "Studies towards the total synthesis of ouabagenin." Canadian Journal of Chemistry 83, no. 6-7 (2005): 728–40. http://dx.doi.org/10.1139/v05-042.

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An anionic cyclization strategy developed in our laboratory was used to produce a versatile and convergent synthesis of an advanced tetracyclic intermediate for the construction of ouabagenin and closely related analogs.Key words: organic chemistry, synthesis, cycloaddition, polycyclization, Michael reaction, DielsAlder reaction, steroids, oubain, ouabagenin, natural products.

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27

Baldwin, Jack E., Alexander V. W. Mayweg, Karin Neumann, and Gareth J. Pritchard. "Studies toward the Biomimetic Synthesis of Tropolone Natural Products via a Hetero Diels−Alder Reaction." Organic Letters 1, no. 12 (1999): 1933–35. http://dx.doi.org/10.1021/ol991067y.

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28

Pasfield, Luke A., Laura de la Cruz, Junming Ho, Michelle L. Coote, Gottfried Otting, and Malcolm D. McLeod. "Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels-Alder Reaction." Asian Journal of Organic Chemistry 2, no. 1 (2013): 60–63. http://dx.doi.org/10.1002/ajoc.201200171.

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29

Heravi, Majid M., and Vaezeh Fathi Vavsari. "ChemInform Abstract: Recent Applications of Intramolecular Diels-Alder Reaction in Total Synthesis of Natural Products." ChemInform 46, no. 32 (2015): no. http://dx.doi.org/10.1002/chin.201532283.

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30

Ward, Dale E., та Yuanzhu Gai. "Synthesis of 10-methyl-Δ4-octalins by Diels–Alder reactions of 2H-thiopyran surrogates for 1-ethenyl-2-methylcyclohexene". Canadian Journal of Chemistry 75, № 6 (1997): 681–93. http://dx.doi.org/10.1139/v97-082.

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Diels–Alder reactions of 1-ethenyl-2-methylcyclohexene derivatives could be a versatile route to a variety of natural product skeletons that possess a 10-methyldecalin substructure with additional substitution at C-8 and C-9. These dienes are unreactive due (in part) to the presence of the vinyl methyl group, which destabilizes the necessary s-cis conformation. The use of 2H-thiopyran diene surrogates for 1-ethenyl-2-methylcyclohexene is investigated. The desired Diels–Alder adducts were not obtained by reaction of 6,7,8,8a-tetrahydro-5,5-dimethyl-3-tris(1-methylethyl)silyloxy-1H-2-benzothiopy

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31

Saito, Naoki, and Paul A. Grieco. "Development of Cationic Diels-Alder Reaction in Highly Polar Media and Total Syntheses of Natural Products." Journal of Synthetic Organic Chemistry, Japan 58, no. 1 (2000): 39–49. http://dx.doi.org/10.5059/yukigoseikyokaishi.58.39.

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32

Wan, Chun Yun, Jun Deng, Hua Liu, Ming Bian, and Ang Li. "ChemInform Abstract: Recent Advances of Intermolecular Diels-Alder Reaction in Bio-Inspired Synthesis of Natural Products." ChemInform 46, no. 9 (2015): no. http://dx.doi.org/10.1002/chin.201509323.

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33

Hooper, Joel F., Jonathan M. White, and Andrew B. Holmes. "Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins." Australian Journal of Chemistry 67, no. 9 (2014): 1189. http://dx.doi.org/10.1071/ch14030.

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The intramolecular Diels-Alder approach to synthesizing eunicellins has proved to be a powerful method for the synthesis of this class of natural products. The key to the success of this strategy is control over the endo/exo selectivity of the cycloaddition reaction, which we have addressed through an organocatalytic reaction employing the MacMillan imidazolidinone catalyst. This approach has been further developed to address the issue of functionality at the C8 position, and a novel scalable method for the extension of the medium-ring lactone has been developed.

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34

Heravi, Majid M., Tahereh Ahmadi, Mahdieh Ghavidel, Bahareh Heidari, and Hoda Hamidi. "ChemInform Abstract: Recent Applications of the Hetero Diels-Alder Reaction in the Total Synthesis of Natural Products." ChemInform 47, no. 9 (2016): no. http://dx.doi.org/10.1002/chin.201609233.

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35

Hall, Dennis G., Renate Müller, and Pierre Deslongchamps. "Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part II: Evidence for unsymmetrical transition states in the formation of A.B.C.[6.6.7] tricyclic products." Canadian Journal of Chemistry 73, no. 10 (1995): 1695–710. http://dx.doi.org/10.1139/v95-208.

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In the preceding paper (Part I) we described the preparation of 10 model TTT and TTC cyclopentadecatrienes. Their conversion to A.B.C.[6.6.7] tricyclic products via a transannular Diels–Alder (TADA) reaction and the analysis of the resulting diastereoselection along with proofs of structures are described in the present article (Part II). The required temperature of reaction was significantly higher (~100 °C) in comparison to that required for the 14-membered lower homologs, indicating that proximity effects are playing a key role in the TADA reaction. The presence of ester groups in the chain

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36

Banwell, Martin G., and Gwion J. Harfoot. "A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene." Australian Journal of Chemistry 57, no. 9 (2004): 895. http://dx.doi.org/10.1071/ch04131.

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The enantiomerically pure cis-1,2-dihydrocatechol 3, which is obtained in quantity by microbial dihydroxylation of toluene, has been converted over ten steps, including an initial Diels–Alder cycloaddition reaction, into the tricyclic ketone 12. Direct irradiation of a benzene solution of the latter compound affords a mixture of compounds 13 and 14 which embody the tricyclic frameworks of the sesquiterpene natural products tsugicoline A (1) and isovelleral (2), respectively.

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37

Li, Xiang, Xiaojin Zhang, Zhuoqin Yu, Xiaorong Liu, Qidong You, and Qinglong Guo. "Microwave-Assisted Claisen Rearrangement/Diels–Alder Cascade reaction for the Synthesis of Caged Garcinia Natural Products and Analogues." Journal of Chemical Research 35, no. 11 (2011): 630–33. http://dx.doi.org/10.3184/174751911x13191290708355.

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38

Zhi-Yu, Liu, and Chu Zin-Jie. "Natural products synthesis by retro Diels-Alder reaction III total synthesis of (±)-chromomoric acid D I methyl ester." Tetrahedron Letters 34, no. 2 (1993): 349–52. http://dx.doi.org/10.1016/s0040-4039(00)60585-3.

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39

Saito, Naoki, and Paul A. Grieco. "ChemInform Abstract: Development of Cationic Diels-Alder Reaction in Highly Polar Media and Total Syntheses of Natural Products." ChemInform 32, no. 3 (2001): no. http://dx.doi.org/10.1002/chin.200103288.

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40

Constantino, Andre F., Carla S. Francisco, Diana C. Cubides-Roman, and Valdemar Lacerda. "Hetero-Diels-Alder Reactions in the Synthesis of Biologically Active Nitrogen Compounds: A Review." Current Organic Synthesis 15, no. 1 (2018): 84–104. http://dx.doi.org/10.2174/1570179414666170517170230.

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Background: The Hetero-Diels-Alder reaction (HDAR) is a method extensively used in organic chemistry as a tool in the synthesis of innumerous polycyclic compounds in particular nitrogen compounds, presents in many natural products, medicinally relevant substances and organic materials. The literature describes innumerable studies of HDAR using classic methods and modern developments such as reactions on the solid phase, the use of catalysts, transformations in aqueous solution and under microwaves. Objective: This review describes a variety of HDAR focused on obtaining nitrogen-containing comp

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41

Hilvert, Donald. "Engineering Enzymes and Antibodies." MRS Bulletin 17, no. 11 (1992): 48–52. http://dx.doi.org/10.1557/s0883769400046662.

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Phenomenal rate accelerations, exacting selectivities, and mild reaction conditions characterize biocatalysis and have generated considerable interest in nonbiological applications of enzymes. As a result of greater availability and purity, these molecules are now being used increasingly in organic synthesis to prepare complex natural products and novel materials. They are also being exploited industrially in the production of food additives, pharmaceuticals, and fine chemicals.Unfortunately, for many commercial applications, natural enzymes may be unsuitable. They may be unstable or difficult

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42

Carosso, Serena, and Marvin J. Miller. "ChemInform Abstract: Nitroso Diels-Alder (NDA) Reaction as an Efficient Tool for the Functionalization of Diene-Containing Natural Products." ChemInform 45, no. 45 (2014): no. http://dx.doi.org/10.1002/chin.201445265.

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43

Faizullina, Liliya Kh, Yulia S. Galimova, Yulia A. Khalilova, and Farid A. Valeev. "Diels-Alder adduct of levoglucosenone with diene Dane approaches to estrogens." Butlerov Communications 62, no. 6 (2020): 20–25. http://dx.doi.org/10.37952/roi-jbc-01/20-62-6-20.

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Levoglucosenone has established itself as a good Michael acceptor and a powerful dienophile in Diels-Alder reactions, dipolar cycloaddition and in a number of other transformations. In the Diels-Alder reactions of levoglucosenone with 1,3-dienes, chiral derivatives of cyclohexene are obtained, which are valuable products for the synthesis of natural compounds. We previously studied the reaction of the interaction of levoglucosenone with Dane diene under catalytic, thermal conditions, at ultrahigh pressures and microwave irradiation. It was found that as a result of the reaction, 2 adducts are

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44

Zhi-Yu, Liu, and Chu Xin-Jie. "Natural products synthesis by retro Diels-Alder reaction V stereospecific synthesis and structural revision of (±)-chromomoric acid Cl methyl ester." Tetrahedron Letters 34, no. 24 (1993): 3885–88. http://dx.doi.org/10.1016/s0040-4039(00)79254-9.

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45

Li, Xiang, Xiaojin Zhang, Zhuoqin Yu, Xiaorong Liu, Qidong You, and Qinglong Guo. "ChemInform Abstract: Microwave-Assisted Claisen Rearrangement/Diels-Alder Cascade Reaction for the Synthesis of Caged Garcinia Natural Products and Analogues." ChemInform 43, no. 16 (2012): no. http://dx.doi.org/10.1002/chin.201216205.

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46

Banwell, Martin G., Malcolm D. McLeod, and Andrew G. Riches. "Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine—Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring." Australian Journal of Chemistry 57, no. 1 (2004): 53. http://dx.doi.org/10.1071/ch03161.

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In connection with efforts to develop an efficient total synthesis of the biologically active natural product taxinine 1, the enzymatically-derived and monochiral cis-1,2-dihydrocatechol 7 was converted, over several steps including a Diels–Alder cycloaddition reaction, into the bicyclo[2.2.2]octan-2-one 18. Reaction of the last compound with the organocerium reagent 22 afforded the 1,5-diene 23 which engaged in an anionic oxy-Cope rearrangement reaction to give, after C-methylation of the product enolate 25, bicyclo[5.3.1]undecenone 27 embodying the AB-ring system of target 1. Two methods for

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47

Caygill, Graham B., David S. Larsen, and Brett S. McFarlane. "Synthetic Approaches to the Angucycline Antibiotics: A Synthesis of (±)-Hatomarubigin B and C." Australian Journal of Chemistry 50, no. 4 (1997): 301. http://dx.doi.org/10.1071/c96106.

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The synthesis of the angucycline natural products hatomarubigin B and C in racemic form is described. The key step in the construction of the benz[a]anthraquinone skeleton of these molecules was the Diels–Alder reaction of the acetate of (E,1R*,5R*)-3-(2′-methoxyvinyl)-5-methylcyclohex-2-en-1-ol and 5-acetoxy-8-hydroxy-1,4-naphthoquinone. Methylation of the C11 phenolic group of the resulting cycloadduct, followed by aromatization of the B ring with subsequent deacylation gave (±)-hatomarubigin C. Oxidation of the latter compound with Dess-Martin periodinane, 1,1,1-triacetoxy-1,1-dihydro-1,2-b

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48

Roscales, Silvia, and Joaquín Plumet. "Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry." Natural Product Communications 12, no. 5 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200517.

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Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Di

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Heravi, Majid M., Mahzad Dehghani, Vahideh Zadsirjan, and Manijheh Ghanbarian. "Alkynes as Privileged Synthons in Selected Organic Name Reactions." Current Organic Synthesis 16, no. 2 (2019): 205–43. http://dx.doi.org/10.2174/1570179416666190126100744.

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Background:Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddti

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Birkett, Stephen L., Darran A. Loits, Samantha Wimala, and Mark A. Rizzacasa. "Synthesis of myxobacteria metabolites." Pure and Applied Chemistry 84, no. 6 (2012): 1421–33. http://dx.doi.org/10.1351/pac-con-11-11-19.

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Myxobacteria are an excellent source of novel secondary metabolites with a range of biological activities. This review details the synthesis of several examples of these natural products. The total synthesis of all the members of the crocacin family is presented where the stereochemistry of the stereotetrad was set via a tin-mediated syn-aldol reaction followed by selective anti-reduction. The other key step in the route to crocacins A, B, and D was the introduction of the enamide functionality by acylation of an enecarbamate. A formal synthesis of apicularen A is also discussed, which involve

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