Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive MC: 0358, La Jolla, California 92093-0358, USA.
Org Lett. 2011 Nov 4;13(21):5854-7. doi: 10.1021/ol202476j. Epub 2011 Oct 5.
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.
报道了一种高效的 norcembrenolide B（8）和 scabrolide D（9）的立体选择性合成方法。该策略的灵感来自于相关cembranoids 的生物发生关系。这一方法的关键是 norbipinnatin J 的构建，它通过选择性的 C2 脱氧和 C8 氧化生成 norrubifolide 和 norcoralloidolide A。然后，通过一系列的选择性氧化和骨架重排，以不同的方式得到化合物 8 和 9。这些研究允许对 scabrolide D（9）的结构进行修正，它与 norcembrenolide C 相同。
