ASYMMETRIC TOTAL SYNTHESIS OF ATISINE VIA INTRAMOLECULAR DOUBLE MICHAEL REACTION

被引：92
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.
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页码：1164 / 1171
页数：8
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