199392-56-8Relevant articles and documents
An epoxide-based enantioselective synthesis of the antifungal antibiotic (+)-preussin
Beier,Schaumann
, p. 1296 - 1300 (2007/10/03)
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.