Two routes were evaluated for the preparation of multiply functionalized cyclohexane derivatives in a stereocontrolled fashion from readily available Hajos–Parrish ketone 1. Reduction (catalytic or dissolving metal) led to the cis-isomer 8, in stark contrast to previous literature. Finally, modification of earlier steroid chemistry allowed the synthesis of the trans-isomer 14. The latter is a useful intermediate for the synthesis of 7-deoxytaxol derivatives.
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 2000|
|MoE publication type||A1 Journal article-refereed|