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 i...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.展开更多
(+)-Preussin (1) and its 5-epimer were synthesized from the divinylcarbinol (3) with Sharpless asymmetric epoxidation of 3 and the oxidative cyclization of 9 with PDC as the key steps.
基金supported by the National Natural Science Foundation of China(21332007)the Program for Changjiang Scholars and Innovative Research Team in University(PCSIRT)of Ministry of Education,China
文摘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.
基金Project supported by the National Natural Science Foundation of China
文摘(+)-Preussin (1) and its 5-epimer were synthesized from the divinylcarbinol (3) with Sharpless asymmetric epoxidation of 3 and the oxidative cyclization of 9 with PDC as the key steps.
