Synthesis of salacinol

Salacinol, a new type of alpha-glucosidase inhibitor discovered from the an tidiabetic herb, was synthesized for the first time. Under the strategy tha t salacinol would be synthesized by the coupling reaction between 1,4-epith io-D-arabinitol and the cyclic sulfate of an erythritol derivative, the mod el coupling reactions between tetrahydrothiophene and versatile cyclic sulf ate derivatives were undertaken. These experiments indicated that the 1,3-d iol of the cyclic sulfate should be protected with the isopropylidene group , otherwise, even the benzylidene-protected cyclic sulfate decomposed durin g the reaction. Thus, the salacinol was synthesized using the cyclic sulfat e of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product wa s deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.