6,19-carbon-bridged steroids. Synthesis of 6,19-methanoprogesterone |
| |
Authors: | Joselevich María Ghini Alberto A Burton Gerardo |
| |
Institution: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, C1428EGA Buenos Aires, Argentina. |
| |
Abstract: | 6,19-Methanoprogesterone (4) was synthesized in nine steps from the readily available 3 beta,20 beta-diacetyloxy-5 alpha-bromo-6,19-oxidopregnane (5) in 14% overall yield. The additional carbon atom was introduced by reaction of a C-19 aldehyde with Ph3PCHOCH3 under salt free conditions and subsequent hydrolysis to give the homologous aldehyde. Intramolecular addition of the newly incorporated carbonyl (C-19a) to the olefinic C-6 in ring B was achieved by means of a Prins reaction with TiCl4 as Lewis acid. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|