Hajos-Parrish ketone: approaches toward C-ring precursors of 7-deoxytaxol

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.