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Recent work has emphasized the importance of C27 bile acids both as evolutionary precursors of the C24 bile acids and as likely intermediates in the biosynthesis of the latter compounds from cholesterol (for reviews see Bergstrom, 1955; Haslewood, 1955). Much of the early work on the C27 and C2. bile acids and alcohols was carried out in Japan, but an acid C27H4,06 was isolated in this laboratory from the bile of various members of the Crocodylidae (Haslewood, 1952a). This was thought to be 3a:7a:12a-trihydroxycoprostanic acid, and was later proved to be a C07 acid by synthesis of the 'stem acid' coprostanic acid, C27H4602, from cholanic acid (Bridgwater & Haslewood, 1952). An acid named 'a.-trihydroxybisnorsterocholanic' acid, m.p. 172°, was isolated from the bile of the frog Rana cate8biana (Kurauti & Kazuno, 1939), and 'p-trihydroxybisnorsterocholanic acid', m.p. 1901950, was later isolated from the same source (Mabuti, 1941). Both these acids were also isolated from the bile of Rana nigromnwcuata nigromuuata (Komatsubara, 1954). The 'oc-trihydroxybisnorsterocholanic acid', m.p. 1720, has been shown to be identical with trihydroxycoprostanic acid isolated from the bile of Alligator mi8i8 ppienai8 (Haslewood, 1952a) and the terms 'oc-' and ',-trihydroxybisnorsterocholanic acid' are now replaced by 'oa-' and 'f, '-trihydroxycoprostanic acid respectively. This earlier work left two further aspects of the problem to be elucidated, namely the position and configuration of the three hydroxyl groups in the trihydroxycoprostanic acids and, more important, the question of isomerism at C-25, since, with the conversion in vivo of the terminal i8opropyl group of the cholesterol side chain into -CHMe .CO2H, a new asymmetric centre is introduced. It was therefore decided to attempt the partial synthesis of the two 3a:7a:12m-trihydroxycoprostanic acids and similar acids with extended side chains (i.e. bile acids in which the -CHMe.CH2-CH2.CO2H chain is lengthened). Some extensions of the side chains of bile acids have been previously reported, thus, ,B-3x:7:12octrihydroxycoprostanic acid, m.p. 1950 (Komatsubara, 1954; Bridgwater, 1955), and bishomocholic acid (Kazuno, Komatsubara & Baba, 1954;

Partial synthesis of the two 3α:7α:12α-trihydroxycoprostanic acids and of similar bile acids with extended side chains