NEW ROUTES TO FUNCTIONALIZED BENZAZEPINE SUBSTRUCTURES - A NOVEL TRANSFORMATION OF AN ALPHA-DIKETONE THIOAMIDE INDUCED BY TRIMETHYL PHOSPHITE

被引:69
作者
FANG, FG
MAIER, ME
DANISHEFSKY, SJ
SCHULTE, G
机构
[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511
[2] YALE UNIV,CTR CHEM INSTRUMENTAT,NEW HAVEN,CT 06511
关键词
D O I
10.1021/jo00290a011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
General protocols for the transformation of substituted dihydroisoquinolines into functionalized benzazepine products are described. An important element involves initial hydrolytic succinoylation of a dihydroisoquinoline to afford a ring-opened intermediate. Subsequent closure to the homologous benzazepine ring is accomplished by condensation of several carbenoid-type equivalents with monothioimide and thioamide carbonyl groups. Application of this methodology to a formal synthesis of cephalotaxine (3) is described. © 1990, American Chemical Society. All rights reserved.
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页码:831 / 838
页数:8
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