Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer

被引:38
作者
East, SP [1 ]
Shao, F [1 ]
Williams, L [1 ]
Joullie, MM [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
alkaloids; macrocycles; strained compounds;
D O I
10.1016/S0040-4020(98)00808-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The naturally occurring cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer were synthesized in 18 steps from D-serine. The key steps in the synthesis were the formation of the alkylaryl ether linkage via all SNAr reaction with 4-fluorobenzonitrile and the macrocyclization to form the 14-membered ring using a modification of the Schmidt protocol involving an activated pentafluorophenyl ester. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:13371 / 13390
页数:20
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