Polycyclic analogues of trans-decalones. Part 4. Synthesis, optical resolution, and circular dichroism of trans-anti-trans-perhydrophenanthren-4-one

Racemic perhydrophenanthren-4-one has been synthesised from the tricyclic enone (±)-(2). The derived saturated axial hydroxy-compound (5), resolved as its 3β-acetoxyandrost-5-ene-17β-carboxylate afforded the (–)-(4aR,4bR,8aS,10aS)-perhydrophenanthren-4-one (1) of high optical purity. C.d. data of (–)-(1), which represents the simplest rigid ketone with a ‘front-octant’ six-membered ring hitherto studied, have been measured and the results are discussed.