The first enantioselective total synthesis of(+)-preussin B and an improved synthesis of(+)-preussin by step-economical methods

摘要

The first enantioselective total synthesis of(+)-preussin B and an improved synthesis of the antifungal alkaloid(+)-preussin are described. Our approach relied on the four step-economical synthetic methods developed in our laboratory:(1) the cis-diastereoselective reductive dehydroxylation of hemiaminals;(2) the direct amide/lactam reductive alkylation;(3) the one-pot N,O-bisdebenzylation-N-methylation; and(4) the one-step synthesis of malimide from malic acid. Both total syntheses are quite concise, which have been achieved in six steps, and gave overall yields of 25.7% and 27.6%, respectively.