Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid

被引：5

作者：

Hethcox, J. Caleb ^{[1
]}

Shanahan, Charles S. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2015年 / 71卷 / 37期

基金：

美国国家卫生研究院;

关键词：

Total synthesis; Conjugate addition; Chiral auxiliary; Cuprate; Succinate; BUTYROLACTONE NATURAL-PRODUCTS; (-)-ROCCELLARIC ACID; ASYMMETRIC-SYNTHESIS; FORMAL SYNTHESIS; (+/-)-DIHYDROPROTOLICHESTERINIC ACID; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; (-)-NEPHROSTERANIC ACID; CHIROSPECIFIC SYNTHESIS; COPPER(II) COMPLEXES;

D O I：

10.1016/j.tet.2015.05.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral gamma-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (-)-dihydroprotolichesterinic acid to date, but several attempts to prepare other succinate-derived natural products, such as pilocarpine and antrodin E, were unsuccessful. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6361 / 6368

页数：8

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