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, , was d-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, , 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.