Synthesis of 1,5-disubstituted-2-hydroxy-gibbatetraen-6-ones

C - Chemistry – Metallurgy – 07 – C

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C07C 45/61 (2006.01) C07C 49/755 (2006.01)

Patent

CA 2585655

1,5-disubstituted-2-hydroxy-gibbatetraen-6-ones are useful as estrogen receptor modulators and as precursors to estrogen receptor modulators. The current invention provides a method for the synthesis of 1,5-disubstituted-2- hydroxy-gibbatetraen-6-ones from simple indanone starting materials via a Robinson-type annulation followed by an internal alkylation reaction. This invention further describes the novel use of a fluoroethyl substituent as a latent alkylating group for an internal cyclization reaction.

Les 2-hydroxy-gibbatétraen-6-ones disubstituées en 1,5 sont utiles en tant que modulateurs du récepteur de l'oestrogène et précurseurs de ces modulateurs. L'invention porte sur un procédé de synthèse des 2-hydroxy-gibbatétraen-6-ones disubstituées en 1,5, à partir d'un matériau de départ de simple indanone par annulation de type Robinson suivie d'une réaction d'alkylation interne. L'invention porte en outre sur une nouvelle utilisation d'un substituant de fluoroéthyle comme groupe alkylisant latent d'une réaction de cyclisation interne.

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