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Steroids XV1. The bromination of 3-ketosteroids of the normal series

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Zusammenfassung

Die Bromwasserstoffabspaltung aus den bisher als 4,4-Dibrom-Verbindungen aufgefaßtennormalen Dibrom-3-ketosteroiden führt zur Bildung von 1,4-Dien-3-onen (IV), welche bisher nur aus 2,4-Dibrom-3-ketoallosteroiden erhalten worden waren. Daneben entstehen kleine Mengen von Δ1-2-Brom-3-ketonormal-steroiden (V). Die Ergebnisse der vorliegenden Arbeit, die überdies durch UV- und Infrarotspektren gestützt sind, machen es äußerst wahrscheinlich, daß die Dibromierung dernormalen 3-Ketosteroide in 2,4-Stellung erfolgt. Die in dieser Arbeit beschriebene Herstellung von 1,4-Dien-3-onen (IV) der Steroid-Reihe erweist sich somit als eine zweite Methode1 zur partiellen Synthese östrogener Hormone, ausgehend von Steroiden dernormalen Serie.

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Steroids XIV:O. Mancera, G. Rosenkranz, andC. Djerassi, J. Org. Chem. (in press).

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Djerassi, C., Rosenkranz, G. Steroids XV1. The bromination of 3-ketosteroids of the normal series. Experientia 7, 93–95 (1951). https://doi.org/10.1007/BF02165553

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Keywords

  • Dibromo
  • Pyridinium Salt
  • Pulegone
  • Collidine
  • Acetic Acid Lead