Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization

Article abstract of DOI:10.1055/s-1997-3270

A cyclobutanone possessing a bicyclo[2.2.1]heptene framework {endo-tricyclo[4.2.1.0^2,5]non-7-en-3-one} has been prepared in both enantiomeric forms employing lipase-mediated kinetic resolution as the key step. To determine the absolute configuration, as well as to demonstrate the synthetic potential, both enantiomers of the cyclobutanone obtained have been transformed enantioconvergently into the key intermediate of the sesquiterpene (+)-β-santalene and the iridoid monoterpene (-)-boschnialactone.