USE OF THE ME3Sn FUNCTION AS A READILY REMOVABLE "ANCHORING" GROUP IN THE SYNTHESIS OF ENANTIOMERICALLY PURE BICYCLIC ALCOHOLS AND KETONES

Article abstract of DOI:10.1016/S0040-4039(00)92348-7

Subjection of (5R,6R)-(-)-3,6-dimethyl-5-trimethylstannyl-2-cyclohexen-1-one (11) to appropriate annulation sequences provides the cis-fused ketones 15, 20, and 21, which, upon reduction (Li, NH3, THF, t-BuOH) are converted smoothly into the enantiomerically pre bicyclic alcohols 16, 22, and 23, respectively.Compound 16 is readily transformed into the unichiral ketones 6 and 7.