An epoxide-based enantioselective synthesis of the antifungal antibiotic (+)-preussin

Article abstract of DOI:10.1055/s-1997-1347

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-amino-alkyl) 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.