We report a stereoselective synthesis of polysubstituted housanes via bismetalated cyclopropane intermediates. The strategy relies on diastereoselective allylzincation of lithiated cyclopropenes followed by intramolecular cyclization, generating metalated housanes as key intermediates. Subsequent electrophile trapping enables efficient diversification of the housanes. Notably, this approach provides access to 2,3-dialkyl-substituted housanes, allowing the selective synthesis of both the diastereomers.
Orbach et al. (Tue,) studied this question.