Enantiospecific synthesis of B-seco-C-aromatic taxanes

摘要

A simple and efficient methodology for the enantiospecific synthesis of B-seco-C-aromatic taxanes starting from monoterpene (R)-carvone is described. Coupling of 6,6-dimethylcarvone 5 with appropriate arylethyl bromides followed by oxidation generates the enones 7, 15, 25, which are transformed into the 20-nor-B-seco-C-aromatic taxane derivatives 11, 17 and B-seco-C-aromatic taxane derivative 29 via degradation of the isopropenyl group.