ASYMMETRIC TOTAL SYNTHESIS OF ATISINE VIA INTRAMOLECULAR DOUBLE MICHAEL REACTION

被引：90

作者：

IHARA, M

SUZUKI, M

FUKUMOTO, K

KABUTO, C

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

[2] TOHOKU UNIV,FAC SCI,INSTRUMENTAL ANALY CTR CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 03期

关键词：

D O I：

10.1021/ja00159a042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The bridged, pentacyclic intermediate 2 for atisine (1) was synthesized in a naturally occurring enantiomeric form from dimethyl cyclohexanone-2,6-dicarboxylate (6). The synthesis is composed of the following key steps: (1) formation of the azabicyclo[3.3.1]nonane by a double Mannich reaction, (2) enantioselective conversion by a lipase-catalyzed acylation, (3) stereoselective hydroboration in the presence of BF3·Et2O, and (4) construction of the bicyclo[2.2.2]octane ring system by an intramolecular double Michael reaction. © 1990, American Chemical Society. All rights reserved.

引用

页码：1164 / 1171

页数：8

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