STEREOCONTROLLED SYNTHESIS OF KEY INTERMEDIATES IN THE TOTAL SYNTHESIS OF ACETOGENINS OF ANNONACEAE

被引：32
作者：
FIGADERE, B
CHABOCHE, C
PEYRAT, JF
CAVE, A
机构：
[1] Laboratoire de Pharmacognosie, associé au CNRS (BIOCIS) Faculté de Pharmacie
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期
关键词：
STEREOSPECIFIC SYNTHESIS; GAMMA-LACTONES; ACETOGENIN; STEREOCHEMICAL RELATIONSHIP ASSIGNMENT;
D O I：
10.1016/S0040-4039(00)61460-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation.
引用
收藏
页码：8093 / 8096
页数：4
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