(-)-外异香豆素的全合成。

Total synthesis of (-)-exiguolide.

机构信息

Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan.

出版信息

Org Lett. 2010 Feb 5;12(3):584-7. doi: 10.1021/ol902778y.

DOI:10.1021/ol902778y

PMID:20063897

Abstract

Total synthesis of (-)-exiguolide, the natural enantiomer, has been accomplished for the first time. The bis(tetrahydropyran) subunit was efficiently synthesized via consecutive olefin cross-metathesis/intramolecular oxa-conjugate addition/reductive etherification. Construction of the 20-membered macrocycle was achieved by Yamaguchi macrolactonization. Stereoselective introduction of the (E,Z,E)-triene side chain via Suzuki-Miyaura coupling completed the total synthesis.

摘要

首次实现了天然对映异构体 (-)-exiguolide 的全合成。通过连续的烯烃交叉复分解/分子内氧杂共轭加成/还原醚化反应，高效合成了双（四氢吡喃）亚基。通过 Yamaguchi 大环内酯化反应构建了 20 元大环。通过 Suzuki-Miyaura 偶联反应立体选择性地引入了 (E,Z,E)-三烯侧链，完成了全合成。