Dehydroisoandrosterone was formylated at C-16 by a Vilsmeier reaction and by condensation with methyl formate. The product of the latter reaction was converted to 16-acetylandrosta-4,16-dien-3-one and its X-ray crystal structure was determined.

Steroids Steroids U 0300The Preparation and Crystal Structure of 16-Acetylandrosta-4,16-dien-3-one. -The synthesis of the title compound (VIII) and its 17-chloro analogue (III) starting with the formylation of dehydroisoandrosterone (I) using a condensation/reduction sequence or Vilsmeier reaction, resp., are described (yields given in g). -(DALMARIS, J.; HANSON*, J. R.; HITCHCOCK, P. B.; KIRAN, I.; J. Chem. Res., Synop. 2003, 3, 150-152; Sch. Chem., Phys. Environ. Sci., Univ. Sussex, Brighton BN1 9QJ, UK; Eng.) -F. Santoso 37-158