Serini Reaction

A. Serini et al., Ber. 72, 391 (1939).

Zinc-promoted rearrangement of 17-hydroxy-20-acetoxysterol derivatives into C-20 ketones; the reaction is applicable to other cyclic, as well as open-chain alcohols:

Reviews: C. W. Shoppe, Chimia 4, 418 (1948); L. F. Fieser, M. Fieser, Steroids (Reinhold Publishing Corp., New York, 1959) p 628; N. L. Wendler in Molecular Rearrangements Part 2, P. de Mayo, Ed. (Wiley-Interscience, New York, 1964) p 1038; E. Ghera, Chem. Commun. 1968, 1639; J. Org. Chem. 35, 660 (1970).