Development of new chiral building blocks for synthesis of bicyclo[3.3.0]octane compounds

Ti(II)-mediated tandem cyclization of (E)-5-(tert-butyldimethylsilyloxy)-8-trimethylsilyl-2-octen-7-ynoate (7) prepared from commercially available optically active epichlorohydrin (2) proceeded diastereoselectively to provide 7-(tert-butyldimethylsilyloxy)-2-trimethylsilylbicyclo[3.3.0]oct-1-en-3-one (1), which serves as a useful chiral building block or intermediate to prepare a variety of compounds having a bicyclo[3.3.0]octane framework.