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
收藏
页码：3707 / 3712
页数：6
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