American Chemical Society
ol202476j_si_003.cif (14.26 kB)

Total Synthesis of Norcembrenolide B and Scabrolide D

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posted on 2011-11-04, 00:00 authored by Alec Saitman, Pauline Rulliere, Steven D. E. Sullivan, Emmanuel A. Theodorakis
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.