Total synthesis of natural (-)-codonopsinine employing stereoselective reduction of quaternary α-hydroxypyrrolidine

Article abstract of DOI:10.1016/0040-4039(96)01042-8

A novel and efficient process is described for the total synthesis of a dihydroxypyrrolidine alkaloid, (-)-codonopsinine in 33% overall yield. The synthetic strategy is based on the stereoselective reduction of an α-hydroxypyrrolidine intermediate, elaborated through asymmetric deoxygenation of a homochiral quaternary α-hydroxylactam.