Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (-)-picropodophyllone

被引：26

作者：

Yoshida, S ^{[1
]}

Yamanaka, T ^{[1
]}

Miyake, T ^{[1
]}

Moritani, Y ^{[1
]}

Ohmizu, H ^{[1
]}

Iwasaki, T ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,LEAD OPTIMIZAT RES LAB,YODOGAWA KU,OSAKA 532,JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(97)00643-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at -100 degrees C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (-)-picropodophyllone (7) were achieved. (C) 1997 Elsevier Science Ltd.

引用

页码：9585 / 9598

页数：14

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