Synthesis of (-)-conduritol F, (+)-conduritol B, cyclophellitol from L- quebrachitol

Article abstract of DOI:10.1246/bcsj.66.3760

The methyl ether of cyclitols with vicinal hydroxyl group was cleaved chemoselectively in preference to both cis-and trans-cyclohexylidene moieties by AlCl₃-n-Bu₄NI to afford parent alcohols in good yields. (-) Conduritol F was prepared from L-quebrachitol, an optically active cyclitol from the serum of rubber trees, in five steps by use of the demethylation reaction. The first chiral synthesis of (+)-conduritol B and the total synthesis of cyclophellitol, a novel β-glucosidase inhibitor, are described.