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Springer Verlag, Science China Chemistry, 3(58), p. 478-482

DOI: 10.1007/s11426-014-5270-0

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

Journal article published in 2015 by Pei-Qiang Huang ORCID, Hui Geng, Yong-Song Tian, Qiu-Ran Peng, Kai-Jiong Xiao ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.