radicamine-b and nectrisine

A short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B is reported. Garner's (R)-aldehyde, prepared from D-serine, was the chiral starting material. The pyrrolidine ring was stereoselectively created in a very efficient way through a five-step, one-pot transformation. In addition, an intermediate of this synthesis was transformed into an intermediate of a previously published synthesis of the potent alpha-glucosidase inhibitor nectrisine.

Topics: Aldehydes; Imino Furanoses; Pyrrolidines; Serine; Stereoisomerism