期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 20, 页码 6386-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja0715142
关键词
-
资金
- NCI NIH HHS [R01 CA090349-08, CA 90349, R01 CA090349-06A1, R01 CA090349, R01 CA090349-07] Funding Source: Medline
We describe a highly convergent and flexible synthesis of the novel antarctic marine metabolite palmerolide A-an effort leading to a reformulation of palmerolide A as ent-24, the enantiomer of the C19,C20-bis-epimer of the original proposed structure 1. Our total synthesis features a highly stereoselective vinylogous Mukaiyama aldol reaction to introduce the C19,C20-stereodiad, an efficient Suzuki cross-coupling to install the endocyclic diene unit, and an intramolecular Horner-Wadsworth-Emmons olefination to close the macrocycle. Starting from fragments 2, 3 (ent-3), and 13 (prepared in five to eight steps each, 38-70% overall yield) the synthesis of the proposed structure 1 and the enantiomer of palmerolide A (24) was completed in an additional 14 steps (22 steps longest linear sequence).
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据