Total synthesis of aspidophytine

被引：36

作者：

Marino, Joseph P. ^{[1
]}

Cao, Ganfeng ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 44期

基金：

美国国家卫生研究院;

关键词：

aspidophytine; haplophytine; aspidosperma alkaloids; quaternary carbon center; chiral vinyl sulfoxide; ketene-lactonization; Marino annulation reaction; enantiospecific; tandem;

D O I：

10.1016/j.tetlet.2006.08.115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of aspidophytine was accomplished by employing a newly developed strategy for the enantiospecific syntheses of aspidosperma alkaloids. The key steps involve a novel ketene-lactonization reaction of a chiral vinyl sulfoxide (Marino annulation reaction) to set up the chiral quaternary carbon center, and a tandem Michael addition-alkylation reaction sequence to form the polycyclic core structure. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：7711 / 7713

页数：3

共 17 条

[1]

BORCH RF, 1968, TETRAHEDRON LETT, V17, P61

[2]

COREY EJ, 1979, TETRAHEDRON LETT, V5, P399

[3] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].