199392-55-7

Upstream product

• 199392-54-6 [(1S,2S)-4-Benzenesulfinyl-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-hex-5-enyl]-carbamic acid benzyl ester 
• 198020-19-8 (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 199392-52-4 ((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester 
• 199392-53-5 [(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-phenylsulfanyl-hex-5-enyl]-carbamic acid benzyl ester 

Downstream Products

• 125356-66-3 (+)-preussin 
• 199392-58-0 (2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 199392-57-9 (2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 199392-56-8 [(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-((2R,3R)-3-hydroxymethyl-oxiranyl)-propyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

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

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.