Optical rotatory dispersion and circular dichroism. Part LXXXI. Optical resolution of trans-1eq-decalol, trans-2eq-decalol, and trans,syn,trans-perhydroanthracen-2eq-ol

Abstract

The trans-decalols named in the title have been resolved by fractional crystallisation of their 3β-acetoxyandrost-5-ene-17β-carboxylates, and converted into trans-decalones of high optical purity. The enamine of (±)-trans-2-decalone condensed with but-3-en-2-one to give, after cyclisation, the enone (11) of the perhydroanthracene series. The derived saturated alcohol (14), resolved as its 3β-acetoxyandrost-5-ene-17β-carboxylate (13), afforded the perhydroanthracen-2-one (3).