Catalytic enantioselective total synthesis of (+)-eucomic acid

被引：11

作者：

Estipona, Benzi I. ^{[1
]}

Pritchett, Beau P. ^{[1
]}

Craig, Robert A., II ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, 1200 E Calif Blvd,MC 101-20, Pasadena, CA 91125 USA

来源：

TETRAHEDRON | 2016年 / 72卷 / 26期

基金：

美国国家卫生研究院;

关键词：

Allylic alkylation; Enantioselective; Eucomic acid; Palladium; Total synthesis; HARRINGTONIA VAR DRUPACEA; (R)-EUCOMIC ACID; DERIVATIVES; (+)-DRAGMACIDIN-F; ALKYLATION; COMPLEXES; ALKALOIDS;

D O I：

10.1016/j.tet.2016.02.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective synthesis of (+)-eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted alpha-hydroxyacid moiety found in the natural product. The protecting group strategy was investigated, and a protecting group manipulation was made without any appreciable deleterious effects in the allylic alkylation reaction. Non-natural (+)-eucomic acid is synthesized in a longest linear sequence of 13 steps. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3707 / 3712

页数：6

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