Ring-expanded analogues of natural oxetanocin

Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.