Syntheses of cystothiazole A and its stereoisomers: importance of stereochemistry for antifungal activity
Syntheses of cystothiazole A and its stereoisomers: importance of stereochemistry for antifungal activity
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DOI：
10.1016/j.tet.2003.10.078
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发表时间：
2004-01-01
期刊：
影响因子：
2.1
通讯作者：
Sakagami, Y
中科院分区：
文献类型：
--
作者：
Ojika, M;Watanabe, T;Sakagami, Y
本文报道了粘细菌抗生素甲硫孢菌素的所有立体异构体的对映体控制全合成。在C4-C5位置的自然顺式立体化学由不对称Evans aldol过程控制，而反式关系由改进的Evans aldol方法引入。以醛醇缩合反应的共同底物--已知醛为起始原料，经9步反应合成了噻丙唑A及其3个立体异构体。所有三种立体异构体即使在cystothiazole A的2500倍剂量下也没有显示出抗真菌活性。(C)2003 Elsevier Ltd.保留所有权利。
The enantiocontrolled total syntheses of all the stereoisomers of a myxobacterial antibiotic, cystothiazole A, are described. The natural syn stereochemistry at the C4-C5 position was controlled by the asymmetric Evans aldol process, whereas the anti relationship was introduced by a modified Evans aldol methodology. Starting with a known aldehyde, the common substrate of the aldol reactions, cystothiazole A and its three stereoisomers were synthesized in 9 steps. All three stereoisomers did not show antifungal activity even at a dosage 2500-fold that of cystothiazole A. (C) 2003 Elsevier Ltd. All rights reserved.