Total synthesis of (-)-pseudolaric acid B

被引：89

作者：

Trost, Barry M. ^{[1
]}

Waser, Jerome ^{[1
]}

Meyer, Arndt ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 47期

关键词：

D O I：

10.1021/ja076165q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the enantioselective synthesis of pseudolaric acid B (1a), a diterpene acid isolated from the bark of Pseudolarix kaempferi Gordon, which displays interesting antifungal, antifertility, and cytotoxic activity against multidrug resistant cell lines. Our synthesis utilizes a highly efficient metal-catalyzed [5 + 2] vinylcyclopropane-alkyne intramolecular cycloaddition to construct the polyhydroazulene core of the natural product. Elaboration to the tricyclic scaffold of the pseudolaric acids was completed with an intramolecular alkoxycarbonyl radical cyclization to form the quaternary center and a highly diastereoselective cerium acetylide addition to a methyl ketone for introduction of the acid side chain.

引用

页码：14556 / +

页数：3

共 26 条

[1] SYNTHESIS OF GAMMA-LACTONES AND DELTA-LACTONES BY FREE-RADICAL ANNELATION OF SE-PHENYL SELENOCARBONATES [J].