Steroid spirolactonization

Details Steroid spirolactonization Steroid spirolactonization

C - Chemistry, Metallurgy

07

J

C07J 75/00 (2006.01) C07J 19/00 (2006.01)

Patent

CA 2519770

A steroid comprising a 17-spirolactone or corresponding open lactone structure is obtained by carbonylation of a 17-alkenyl or 17-alkynyl substrate. A 17- alkenyl intermediate may be prepared by semi-hydrogenation of a 17-alkynyl group. Multiple reaction schemes are disclosed for preparation of a 3-keto- 9,11-epoxy-17-spirolactone steroid such as eplerenone. Novel intermediates are also disclosed, as well as steps for forming such novel intermediates, or converting them to further intermediates or products, by semi-hydrogenation, carbonylation, 6,7-dehydrogenation, furylation or other transformations or combinations thereof.

Un stéroïde comprenant une structure de 17-spirolactone ou une structure ouverte de lactone correspondante est fabriqué par la carbonylation d'un substrat 17-alcényle ou 17-alkynyle. Un intermédiaire 17-alkynyle peut être préparé par la semi-hydrogénation d'un groupe 17-alkynyle. L'invention porte sur des schémas à réactions multiples qui sont destinées à la préparation d'un stéroïde 3-céto-9,11-époxy-17-spirolactone tel qu'un éplérenone. L'invention concerne aussi la fabrication de nouveaux intermédiaires ou leur transformation en d'autres intermédiaires ou produits par la semi-hydrogénation, la carbonylation, la 6,7-deshydrogénation, la furylation ou par d'autres transformations ou leurs combinaisons.

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