Chirospecific syntheses of nitrogen and side-chain-modified anatoxin analogs. Synthesis of (1R)-anatoxinal and (1R)-anatoxinic acid derivatives

…, FJ Sardina, H Rapoport

文献索引：Howard, Michael H.; Sardina, F. Javier; Rapoport, Henry Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2829 - 2838

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被引用次数: 40

摘要

A straightforward and good yielding route to sidechain analogues of the potent neurotoxin and neurotransmitter (+)-anatoxin (1) has been developed. Peroxy acid oxidation of the (sily1oxy) butadiene 43 derived from readily synthesized, optically pure (1R)-t-BOC-anatoxin (42) affords silyloxy ketone 44. Fluorolysis of 44 followed by oxidative cleavage of the resultant cr-hydroxy ketone 45 gives a mixture of a,@ unsaturated acid 46 and ester 41 in ...