Absolute configuration of a polyol fragment of blasticidin A, a specific inhibitor of aflatoxin production.

Abstract

Blasticidin A (1) and aflastatin A (2), Streptomyces metabolites with similar structures, are specific inhibitors of aflatoxin production by Aspergillus parasiticus. The stereochemistry of the polyol fragment of 1 (3a) containing ten chiral centers was elucidated by applying acetonide and MTPA methods to a variety of acetonide derivatives of 3a, which determined the absolute configuration of 3a. By using the similar methods, the absolute configuration of the polyol fragment of 2 (4a) was determined, which was the same as that elucidated by J-based and other chemical methods previously.