Total synthesis of thiangazole

被引：19

作者：

Akaji, K

Kiso, Y

机构：

[1] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan

[2] Kyoto Pharmaceut Univ, Dept Med Chem, Yamashima Ku, Kyoto 6078414, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(99)00604-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for total synthesis of thiangazole (1), a tris-thiazoline-oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3-dimethyl-imidazolidium hexafluorophosphate(CIP)mediated activation. The successive thiazoline/oxazole rings were constructed by TiCl4- mediated cyclodehydration followed by acid-catalyzed Robinson-Gabriel reaction without difficulty. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：10685 / 10694

页数：10

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