Journal
ORGANIC LETTERS
Volume 13, Issue 21, Pages 5854-5857Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol202476j
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Funding
- National Institutes of Health (NIH) [R01 GM081484]
- National Science Foundation for Instrumentation [CHE9709183, CHE0741968]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0741968] Funding Source: National Science Foundation
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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.
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