Stereoselective synthesis of the antifungal antibiotic (+)-preussin

Article abstract of DOI:10.1016/S0040-4020(98)00981-8

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.