Hydroboration of C-arylglucals. Synthesis of the β-C-arylglucoside nucleus of chaetiacandin

Article abstract of DOI:10.1016/S0040-4039(00)97006-0

The hydroborations of the C-arylglucals 3a-c obtained from palladium catalyzed coupling reactions, provide the corresponding β-C-arylglucosides. Depending upon the conditions chosen for the oxidative workup, either the alcohols 5a-c or the products resulting from silyl migration (4a-c) are readily obtained. The palladium catalyzed coupling-hydroboration sequence has been applied to the synthesis of the β-C-arylglucoside nucleus of chaetiacandin, an anti-yeast antibiotic of the papulacandin family.