An efficient procedure for the synthesis of otherwise difficult to access 17α-amino derivatives of the digitalis series is described. The key reaction is the stereospecific thermocyclisation of 3β-acetoxy-l7β-azidocarbonyloxymethyl-5β-androstan-14β-ol 3b to (17R)-3β-acetixy-14β-hydroxyspiro[5β-androstane-17,4′-oxazolidin]-2′-one 4.
G. Fedrizzi, L. Bernardi, G. Marazzi, P. Melloni and M. Frigerio, J. Chem. Soc., Perkin Trans. 1, 1995, 1755 DOI: 10.1039/P19950001755
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