Total synthesis of the trehalase inhibitors trehalostatin and trehazolin, and of their diastereoisomers. Final structural confirmation of the inhibitor

Abstract

Potent trehalase inhibitors 1–4 have been synthesized, thereby establishing both the structure and the absolute configuration of the known inhibitor trehazolin 2. Compound 1, previously proposed as the structure of trehalostatin, and its diastereoisomer 3, have been shown not to possess any observable inhibitor activity against trehalase. These results indicate that the initial structure assigned for trehalostatin is incorrect, and that its structure is identical with that of trehazolin 2.