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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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Published in: | Organic letters 2011-11, Vol.13 (21), p.5854-5857 |
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container_title | Organic letters |
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creator | Saitman, Alec Rulliere, Pauline Sullivan, Steven D. E Theodorakis, Emmanuel A |
description | 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. |
doi_str_mv | 10.1021/ol202476j |
format | article |
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source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
subjects | Diterpenes - chemical synthesis Models, Molecular Molecular Structure Oxidation-Reduction Stereoisomerism |
title | Total Synthesis of Norcembrenolide B and Scabrolide D |
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