A NEW EFFICIENT SYNTHESIS OF (S)-DOLAPHENINE ((S)-2-PHENYL-1-(2-THIAZOLYL)ETHYLAMINE), THE C-TERMINAL UNIT OF DOLASTATIN-10

被引：60

作者：

IRAKO, N ^{[1
]}

HAMADA, Y ^{[1
]}

SHIOIRI, T ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,TANABE DORI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)88264-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.

引用

页码：7251 / 7264

页数：14

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