Enantioselective synthesis of the hexahydronaphthalene nucleus of (+)-Compactin from ethyl (1R,2S)-2-methyl-4-oxo-cyclohexanecarboxylate and 2-(3-nitropropyl-1,3-dioxolane as four carbon annelating reagent

An enantioselective approach to the synthesis of compactine is described. The key elements of the synthesis are: the preparation of the chiral starting matherial through the enzimatic resolution of a ready avalable carboxylic acid; the introduction of the duoble bond by a Pd(II)-catalized dehydrosilylation ; the construction of a new six-memb-membered ring into the preexisting C-C skeleton.