A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin

Article abstract of DOI:10.1016/0957-4166(96)00009-2

An efficient and novel process is described for the asymmetric synthesis of (2S, 3S, 5R)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin employing reductive deoxygenation of a functionalized quaternary α-hydroxy N-Boc pyrrolidine obtained by stereocontrolled elaboration of tri-O-benzyl-β-D-arabinofuranose. The synthetic strategy involves no separation of stereoisomers through the entire sequence.