Stereospecific Biocatalytic Synthesis of Pancratistatin Analogues
A two-stage enzymatic sequence of dihydroxylation (at the site labelled in yellow) and aldolization (blue) reactions, which has been developed for the synthesis of analogues of the cytotoxic pancratistatin pharmacophore, converts a naphthalene core into a hybrid arene-carbohydrate structure, with simultaneous creation of four contiguous stereocenters. From the multitude of possible equilibrating product isomers, mild bromine oxidation locks the carbohydrate chain into fixed bicyclic lactones of high molecular complexity.
Phung, Anh Nga,Zannetti, Maria Teresa,Whited, Gregg,Fessner, Wolf-Dieter