Synthesis of 16-Oxygenated steroids

Abstract

Since the development of methods for studying the tissue metabolism of testosterone (8), many investigators attempted to isolate and identify the catabolic products of testosterone degradation by various tissues. Reported isolation of 16 alpha-hydroxylated compound (14) opened a new pathway of investigation. Various investigators (5, 14, 17, 19, 22, 24) have since either reported the isolation of other C-16 oxygenated compounds, or have speculated their presence. In view of these observations, it was felt that an attempt should be made to prepare 16-oxygenated derivatives of 17-ketosteroids with the thought that some of the polar compounds isolated in the metabolic studies of Wotiz, Wotiz and Lemon, and Ofner might be steroids substituted at this position. Various syntheses for substitution at the c-16 position have been developed, particularly by Huffman and Lott (26, 33, 34, 35, 36, 37). Recently, Leeds et al. presented a method for the introduction of a C-16 ketone or hydroxyl group (1). This method was the one followed in this work.