Total Synthesis of Norcembrenolide B and Scabrolide D

An efficient stereoselective synthesis of norcembrenolide B (8) and scabrolide D (9) is reported. The strategy is inspired by biogenetic relationships of related cembrenoids. Central to this approach is the construction of norbipinnatin J which upon selective C2 deoxygenation and C8 oxygenation prod...

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Bibliographic Details
Published in:Organic letters 2011-11, Vol.13 (21), p.5854-5857
Main Authors: Saitman, Alec, Rulliere, Pauline, Sullivan, Steven D. E, Theodorakis, Emmanuel A
Format: Article
Language:English
Subjects:
Diterpenes - chemical synthesis
Models, Molecular
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:An efficient stereoselective synthesis of norcembrenolide B (8) and scabrolide D (9) is reported. The strategy is inspired by biogenetic relationships of related cembrenoids. Central to this approach is the construction of norbipinnatin J which upon selective C2 deoxygenation and C8 oxygenation produces norrubifolide and norcoralloidolide A. A sequence of site-selective oxidations and skeletal reorganizations then yields, in a divergent manner, compounds 8 and 9. The studies allow revision of the proposed structure of scabrolide D (9), which is identical to norcembrenolide C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202476j