Synthesis of samanine
Abstract
The salamander alkaloid samanine (3-aza-A-homo-5β-androstan-16β-ol) has been synthesized in 10 steps from testosterone acetate in 17% overall yield, the transposition of the oxygen functionality from C-17 to C-16 being achieved by an elimination–hydroboration–oxidation sequence, and the A-ring expansion and insertion of nitrogen via a Schmidt reaction.