SYNTHESIS OF (-)-(6R)-TETRAHYDRO-6-[(Z-PENT-2-ENYL]-2H-PYRAN-2-ONE AND (+)-(6S)-TETRAHYDRO-6-[(Z)-PENT-2-ENYL]-2H-PYRAN-2-ONE, LACTONES FROM JASMINUM-GRANDIFLORUM L AND FROM POLIANTHES-TUBEROSA L

被引：12

作者：

BLASER, F ^{[1
]}

DESCHENAUX, PF ^{[1
]}

KALLIMOPOULOS, T ^{[1
]}

JACOTGUILLARMOD, A ^{[1
]}

机构：

[1] UNIV NEUCHATEL,INST CHIM,51 AVE BELLEVAUX,CH-2000 NEUCHATEL,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 04期

关键词：

D O I：

10.1002/hlca.19910740412

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-(2S)-Ethyl 2-hydroxyhexanedioate ((2S)-2) was obtained by kinetic resolution of racemic ethyl 2-hydroxyhexanedioate with baker's yeast. The key intermediates (+)-(5R)- and (-)-(5S)-ethyl 5,6-epoxyhexanoate ((5R)-and (5S)-6, resp.) are proved to be useful synthons for the total synthesis of chiral 6-alkyl-delta-lactones, as exemplified by the preparation of both enantiomers of jasmine lactone ((6R)- and (6S)-10, resp.).

引用

页码：787 / 790

页数：4