Stereoselective synthesis of a new methyl-substituted inositol derivative

Abstract

The stereoselective synthesis of methyl-substituted inositol derivative is described. Diene diacetate which is a key compound was first prepared via three steps starting from 2-methyl-p-benzoquinone. Osmium-catalyzed regio- and stereoselective dihydroxylation of diene diacetate afforded cis-diol diasetate, which then produced tetra acetate via acetylation with Ac2O-pyridine. Oxidation and acetylation of the other alkene moiety in the compound gave a hexaacetate compound stereoselectively. Finally, the acetate groups were removed by NH3 leading to formation of the desired new methyl-substituted inositol derivative having a muco-inositol-type stereochemical pattern in the six-membered ring. Spectroscopic methods were used for characterization of all synthesized compounds. (C) 2019 Elsevier Ltd. All rights reserved.