SCHEDULED MAINTENANCE
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.
W. A. Cristofoli and M. Benn, J. Chem. Soc., Perkin Trans. 1, 1991, 1825 DOI: 10.1039/P19910001825
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