A concise and stereoselective synthesis of hydroxypyrrolidines: rapid synthesis of (+)-preussin.

A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of β-iminochlorohydrins, which are readily available from β-ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.