Total Synthesis of Norcembrenolide B and Scabrolide D

被引:32
作者
Saitman, Alec [1 ]
Rulliere, Pauline [1 ]
Sullivan, Steven D. E. [1 ]
Theodorakis, Emmanuel A. [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
CORAL SINULARIA-SCABRA; OKINAWAN SOFT CORAL; PSEUDOPTERANE; CEMBRANE; FURANOCEMBRANOLIDES; (+/-)-BIPINNATIN-J; NORDITERPENOIDS; (+)-INTRICARENE; DITERPENOIDS; LEPTOCLADOS;
D O I
10.1021/ol202476j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5854 / 5857
页数:4
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