Asymmetric Total Synthesis of (−)‐Maoecrystal V

Zhang, Wei-Bin; Shao, Wang; Li, Fuzhuo; Gong, Jianxian; Yang, Zhen

doi:10.1002/asia.201500564

Cited by 25 publications

(7 citation statements)

References 74 publications

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“… 2 − 4 As the most structurally complex member within this family of terpenes, it features a densely interlocked array of ring systems nestled within adjacent vicinal quaternary stereocenters (C-9/10, ent -kaurane numbering). The [2.2.2] bicyclic portion of the molecule is a clear signal for the use of the Diels–Alder transform, and thus all successful total syntheses 4 to date have relied on this strategic maneuver ( Figure 1 A). In striking contrast, the biosynthetic route to this system is proposed to arise via an unusual pinacol-type shift of cation 2 ( Figure 1 B).…”

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confidence: 99%

“…The combination of striking structural features and exciting bioactivity exhibited by the ent -kaurane diterpene maoecrystal V ( 1 , Figure B) has attracted extensive interest within the organic community since 2004. − As the most structurally complex member within this family of terpenes, it features a densely interlocked array of ring systems nestled within adjacent vicinal quaternary stereocenters (C-9/10, ent -kaurane numbering). The [2.2.2] bicyclic portion of the molecule is a clear signal for the use of the Diels–Alder transform, and thus all successful total syntheses to date have relied on this strategic maneuver (Figure A). In striking contrast, the biosynthetic route to this system is proposed to arise via an unusual pinacol-type shift of cation 2 (Figure B) .…”

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confidence: 99%

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11-Step Total Synthesis of (−)-Maoecrystal V

2016

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An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (−)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.

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11-Step Total Synthesis of (−)-Maoecrystal V

2016

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“…Additionally, some examples report the creation of four cycles and three or four stereogenic centers (Scheme 45). 157,158 respectively. A regioselective (5+2) cycloaddition process was used for the formation of polyether furanic cores starting from terminal alkenes and the 3-oxido-pyrilium betaine prepared in situ.…”

Section: Scheme 44: Thf Synthesis By Acetal Reductionmentioning

confidence: 97%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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“…The synthesis commenced with the preparation of allylic alcohol 12 , which was readily obtained by the Diels–Alder reaction of propiolic acid methyl ester and subsequent reduction (see Supporting Information) [7] . Allylic alcohol 12 was subjected to Sharpless asymmetric epoxidation to afford epoxide 13 in 84 % yield and 94 % ee [5e, 8] . (Scheme 2).…”

Section: Figurementioning

confidence: 99%

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

Zong

Zhu

et al. 2021

Angewandte Chemie

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An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3‐dicarbonyl radical‐initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica‐gel‐promoted semipinacol rearrangement to form the 6‐oxabicyclo[3.2.1]octane skeleton and the Suzuki–Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.

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Asymmetric Total Synthesis of (−)‐Maoecrystal V

Cited by 25 publications

References 74 publications

11-Step Total Synthesis of (−)-Maoecrystal V

11-Step Total Synthesis of (−)-Maoecrystal V

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

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