6,19-carbon-bridged steroids. Synthesis of 6,19-methanoprogesterone

6,19-carbon-bridged steroids. Synthesis of 6,19-methanoprogesterone

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 subseque...

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Veröffentlicht in:Organic & biomolecular chemistry 2003-03, Vol.1 (6), p.939-943
Hauptverfasser: Joselevich, María, Ghini, Alberto A, Burton, Gerardo
Format: Artikel
Sprache:eng
Schlagworte:
Models, Chemical
Molecular Structure
Progesterone - analogs & derivatives
Progesterone - chemical synthesis
Steroids - chemical synthesis
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b211974a