The absolute stereochemistry of Wieland–Miescher ketone analogues bearing an angular protected hydroxymethyl group

Abstract

The Wieland–Miescher ketone analogues (3) and (4), each bearing an angular protected hydroxymethyl group, have been prepared by the amino-acid catalysed cyclisation of their cyclohexane-1,3-dione derivatives (1) and (2); the optical purities and absolute configurations of (3) and (4) have been determined by applying the methoxy (trifluoromethyl)phenylacetate method and the c.d. exciton chirality method, respectively, to their mono-9-ol derivatives.