An acyl radical initiated tandem 7-endo/5-exo radical cyclization approach to enantiomerically pure bicyclo[5.3.0]decan-2-ones

Article abstract of DOI:10.1016/S0040-4039(00)91564-8

The preparation of acetonide derivatives of erythro and threo 4,5-dihydroxyhept-6-enoic acids from the chiral pool is described. The phenylseleno esters derived from these acids undergo cyclization with tributyltin hydride to give mixtures of cyclohexanones and cycloheptanones. The inclusion of the appropriate four carbon side chain at C-7 leads, via a tandem radical cyclization process, to the title compounds in moderate yield.