DEHYDROAMINO ACID-DERIVATIVES FROM D-ARABINOSE AND L-SERINE - SYNTHESIS OF MODELS FOR THE AZINOMYCIN ANTITUMOR ANTIBIOTICS

被引:54
作者
MORAN, EJ [1 ]
TELLEW, JE [1 ]
ZHAO, ZC [1 ]
ARMSTRONG, RW [1 ]
机构
[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024
关键词
D O I
10.1021/jo00079a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of aldehydes 17 from D-arabinose and 31 from L-serine provided key precursors for the generation of highly functionalized dehydroamino acid derivatives upon condensation with glycyl phosphonates. Subsequent bromination and intramolecular addition/elimination afforded the azabicyclo[3.1.0]hex-2-ylidene ring system postulated to exist in the azinomycin antitumor antibiotics.
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页码:7848 / 7859
页数:12
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