Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of alpha-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

The single-step construction of various densely oxygenated carboskeletons was achieved by radical-based two- and three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/O-2-mediated decarbonylation readily converted alpha-alkoxyacyl tellurides to alpha-alkoxy carbon radicals, which intermolecularly added to glyoxylic oxime ether or enones to provide the two- component adducts. Furthermore, the three-component adducts were produced by an intermolecular aldol reaction between the aldehyde and the boron enolates generated by capture of the two-component radical intermediates by Et3B. This powerful coupling method serves as a novel strategy for the convergent synthesis of polyol natural products.