Catalytic reduction of 3β-hydroxyandrost-4-ene-17-one with tritium. I. The distribution and configuration of label in 3β-hydroxy-5α-androstane-17-one (1)

✍ Scribed by Yusuf J. Abul-Hajj

• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: French
• Weight: 349 KB
• Volume: 7
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2590070106

✦ Synopsis

Catalytic reduction of 3j3-hydroxyandrost-4-ene-l7-one (I) with tritium gas gave a mixture of 3B-hydroxy-5a-androstane-17-one (11) and 3~-hydroxy-5cc-androstane-l7-one ( 1 1 1 ) . Oxidation of compound 1 1 followed by alkaline equilibration resulted in 37 % loss of label from position 4. 5a-Androstane-3,17-dione (Wa) was converted via the 2,4-dibromide to androst-ll-ene-3,17-dione (V1IIa) with 43 loss of radioactivity from position 5. Chloranil dehydrogenation and alkaline equilibration experiments have shown that the additional label was at C-6a. The distribution and configuration of label in compound 11 was found to be 37 % 4a, 43 5a and 20 % da.