Stereoselective syntheses of cis- and trans-isomers of alpha-hydroxy-alpha,beta-dibenzyl-gamma-butyrolactone lignans: New syntheses of (+/-)-trachelogenin and (+/-)-guayadequiol

被引：37

作者：

Moritani, Y

Fukushima, C

Ukita, T

Miyagishima, T

Ohmizu, H

Iwasaki, T

机构：

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

[2] TANABE SEIYAKU CO LTD, RES & DEV PLANNING DIV, YODOGAWA KU, OSAKA 532, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 20期

关键词：

D O I：

10.1021/jo9601932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cis- and trans-isomers of alpha-hydroxy-alpha,beta-dibenzyI-gamma-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of alpha-benzyl-gamma-butyolactone derivatives 1l-o and 3 as a key step, This method was applied to the syntheses of (+/-)-trachelogenin and (+/-)-guayadequiol, representative examples of the trans- and cis-isomers of alpha-hydroxy-alpha,beta-dibenzyl-y-butyrolactone lignan series.

引用

页码：6922 / 6930

页数：9

共 36 条

[1]

AYRES DC, 1990, LIGNANS

[2] TOTAL SYNTHESIS OF (+/-)-WIKSTROMOL [J].