Total synthesis of (+)-crocacin A

被引：25

作者：

Chakraborty, TK ^{[1
]}

Laxman, P ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 27期

关键词：

antifungal; cytotoxin; aldol reaction; Peterson olefination; enamide; crocacin;

D O I：

10.1016/S0040-4039(03)01171-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin A is described. The crucial (Z)-5,6-enoic amide moiety in this molecule was built by stereoselective partial reduction of a skipped diyne precursor. The diene, thus obtained, was transformed into a silyl epoxide that was regioselectively opened with an azide ion to furnish an alpha-azido-beta-hydroxyalkylsilane intermediate. Peterson elimination of this beta-hydroxysilane component in the final step resulted in the formation of the (Z)-8,9-enamide moiety of the molecule leading to a successful completion of its total synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4989 / 4992

页数：4

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