Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A

被引:52
作者
Decicco, CP
Grover, P
机构
[1] Chemical and Physical Sciences, Dupont Merck Pharmaceutical Company, Experimental Station, Wilmington
关键词
D O I
10.1021/jo952123l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.
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页码:3534 / 3541
页数:8
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