Total synthesis of (+)-crocacin C

被引：37

作者：

Chakraborty, TK ^{[1
]}

Jayaprakash, S ^{[1
]}

Laxman, P ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Bioorgan Lab, Organ Div 111, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2001年 / 57卷 / 46期

关键词：

antifungals; cytotoxins; aldol reactions; katsuki-sharpless reactions;

D O I：

10.1016/S0040-4020(01)00940-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of potent antifungal. and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S,7S,8R,9S) configuration. While C8 and C9 stereocenters were built following a Ti(IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9461 / 9467

页数：7

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