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

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• 作者：Pei-Qiang Huang (1)
  Hui Geng (1)
  Yong-Song Tian (1)
  Qiu-Ran Peng (1)
  Kai-Jiong Xiao (1)
  
  1. Key Laboratory for Chemical Biology of Fujian Province ; Department of Chemistry ; College of Chemistry and Chemical Engineering ; Xiamen University ; Xiamen ; 361005 ; China
  
• 关键词：total synthesis ; (+) ; preussin B ; step ; economical methods ; reductive alkylation ; lactams ; pyrrolidine alkaloids
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2015
• 出版时间：March 2015
• 年：2015
• 卷：58
• 期：3
• 页码：478-482
• 全文大小：400 KB
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• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chinese Library of Science
  Chemistry
  
• 出版者：Science China Press, co-published with Springer
• ISSN：1869-1870

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.