Synthesis of aminocyclitol moieties of trehalase inhibitors, trehalostatin and trehazolin. Correct structure of the inhibitor

Abstract

The respective aminocyclitol moieties 3a and 4a of trehalostatin 1 and trehazolin 2, potent trehalase inhibitors, are synthesized as the N,O-pentaacetyl derivatives 3b and 4b in racemic form, in order both to establish the structure of the inhibitor and to provide a synthon useful for its total synthesis.