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Synthesis 1997; 1997(11): 1296-1300
DOI: 10.1055/s-1997-1347
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An Epoxide-Based Enantioselective Synthesis of the Antifungal Antibiotic (+)-Preussin

Christian Beier, Ernst Schaumann*
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany, Fax +49(5323)722858; E-mail: ernst.schaumann@tu-clausthal.de
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Publication Date:
31 December 2000 (online)

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The enantioselective total synthesis of (2S,3S,5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin 1, from (S)-phenylalanine is described. Key steps involve ring-opening of a (1-aminoalkyl)epoxide 5 by an allyl anion, [2,3]-sigmatropic rearrangement of 9 and cyclization of aminoepoxide 11 to give the pyrrolidine unit 12 with the correct stereochemistry.

amino epoxide - allyl anion - [2,3]-sigmatropic rearrangement - Sharpless epoxidation - preussin

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