Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of ent-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B

被引:203
作者
Itoh, Takahiko [1 ]
Ishikawa, Hayato [1 ]
Hayashi, Yujiro [1 ,2 ]
机构
[1] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Res Inst Sci & Technol, Shinjuku Ku, Tokyo 1628601, Japan
关键词
BRYOZOAN AMATHIA-CONVOLUTA; ENANTIOSELECTIVE SYNTHESIS; MICHAEL REACTION; IL-6; ACTIVITY; ORGANOCATALYSIS; ALDEHYDES; DIARYLPROLINOL; KETONES; ETHERS; (R)-CONVOLUTAMYDINE;
D O I
10.1021/ol901432a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hydroxyindole alkaloids. Short syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B have been accomplished.
引用
收藏
页码:3854 / 3857
页数:4
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