219969-17-2

Upstream product

• 219969-14-9 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formylmethyl-1,3-oxazolidine 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 129778-81-0 (1S,2S)-(tert-butoxy)-N-[2-hydroxy-1-benzylpent-4-enyl]carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124-63-0 methanesulfonyl chloride 
• 219969-15-0 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(2-hydroxyundecyl)-1,3-oxazolidine 

Downstream Products

• 158527-21-0 tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Stereoselective synthesis of the antifungal antibiotic (+)-preussin

A concise total synthesis of enantiopure (+)-preussin (1) from L- phenylalanine (3) is described. The key steps involve i) syn-selective formation of the 1,2-amino alcohol fragment 2, via chelation controlled addition of allylmagnesium bromide to N-Boc-phenylalaninal, and ii) L- selectride mediated stereoselective reduction of the ketone 8 to the alcohol derivative 9 with the required stereochemistry for final cyclization.