Two routes were evaluated for the preparation of multiply functionalized cy
clohexane derivatives in a stereocontrolled fashion from readily available
Hajos-Parrish ketone 1. Reduction (catalytic or dissolving metal) led to th
e cis-isomer 8, in stark contrast to previous literature. Finally, modifica
tion 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.