NATURALLY-OCCURRING LINEAR FUSED THIAZOLINE-THIAZOLE CONTAINING METABOLITES - TOTAL SYNTHESIS OF (-)-DIDEHYDROMIRABAZOLE-A, A CYTOTOXIC ALKALOID FROM BLUE-GREEN-ALGAE

被引:42
作者
PATTENDEN, G
THOM, SM
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 14期
关键词
D O I
10.1039/p19930001629
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise total synthesis of the thiazoline-thiazole containing metabolite didehydromirabazole A 1 is described. The synthesis uses the unusual amino acid (R)-2-methylcysteine 20 in sequential cyclocondensations with imino ethers as key steps, viz 22 --> 32 and 37 --> 38.
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页码:1629 / 1636
页数:8
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