Preparation of Versatile Synthetic Precursors of Optically Active 5a‐Carba‐sugars from (−)‐vibo‐Quercitol

Abstract

The spiro‐epoxide derived from (−)‐2‐deoxy‐scyllo‐inosose was converted into the iodide 2, which was directly subjected to elimination conditions, affording the key methylene compound 4. Successive cyclohexylidenation of the tetrol obtained from 4, selective benzoylation, and conventional tosylation gave the homoallyl tosylate 11, which would be a versatile intermediate for preparation of biologically active 5a‐carbahexopyranosylamines and their unsaturated congeners.