Stereoselective synthesis of a versatile intermediate for the total synthesis of mono- and bis-THF containing annonaceous acetogenins

被引：18

作者：

Jan, ST

Li, KQ

Vig, S

Rudolph, A

Uckun, FM ^{[1
]}

机构：

[1] Hughes Inst, Drug Discovery Program, Roseville, MN 55113 USA

[2] Hughes Inst, Dept Chem, Roseville, MN 55113 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(98)02222-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of epoxy tetrahydrofuran (THF) 1, a versatile synthetic precursor for mono-THF and bis-THF containing annonaceous acetogenins, is reported. Compound 1 was synthesized from tridecanal in 11 steps with an overall yield of 24%. The requisite configurations of the stereogenic centers in 1 were established by Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation. Formation of the THF-ring unit was accomplished by acid catalyzed epoxide ring opening and 5-exo cyclization reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：193 / 196

页数：4

共 19 条

[1]

Cave A, 1997, Fortschr Chem Org Naturst, V70, P81

[2] ANNONACEOUS ACETOGENINS - AN UPDATED REVIEW [J].