LIGNANES .11. PREPARATION OF (R)-(+)-BETA-VANYLLYL-GAMMA-BUTYROLACTONE AND ITS USE IN TOTAL SYNTHESIS OF NATURAL LIGNANES

被引：17

作者：

DAUGAN, A ^{[1
]}

BROWN, E ^{[1
]}

机构：

[1] FAC SCI LE MANS,SYNTH TOTALE PROD NAT LAB,URA 482,ROUTE LAVAL,BP 535,F-72017 LE MANS,FRANCE

来源：

JOURNAL OF NATURAL PRODUCTS | 1991年 / 54卷 / 01期

关键词：

D O I：

10.1021/np50073a008

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Condensation of vanillin with dimethyl succinate (using LiOMe) gave the ethylenic hemiester 3. Hydrogenation of 3 gave (R,S)-4. The latter was resolved into both its enantiomers by means of (+)-alpha-methylbenzylamine. Ca(BH4)2 reduction of (R)-(+)-4 and (S)-(-)-4 gave the corresponding beta-vanillyl-gamma-butyrolactones (R)-(+)-1 and (S)-(-)-1, respectively. The lactone (R)-(+)-1 was used for the total syntheses of five naturally occurring and optically active lignans such as (-)-anhydrosecoisolariciresinol [16] and (+)-isolariciresinol [20].

引用

页码：110 / 118

页数：9