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Synthesis 1997; 1997(11): 1296-1300
DOI: 10.1055/s-1997-1347
DOI: 10.1055/s-1997-1347
paper
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An Epoxide-Based Enantioselective Synthesis of the Antifungal Antibiotic (+)-Preussin
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synthesis/199711/lookinside/thumbnails/10.1055-s-1997-1347-1.jpg)
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