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.

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页码：8093 / 8096

页数：4

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