Crystal structures of 10alpha-gon-5-enes from the synthetic pathway to desogestrel |
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Authors: | Modica Emilia Colombo Diego Ronchetti Fiamma Scala Antonio Bombieri Gabriella Marchini Nicoletta Toma Lucio |
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Institution: | Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, 20133 Milano, Italy. |
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Abstract: | X-ray crystallographic studies performed on the product of the ketalization reaction of 13beta-ethyl-11alpha-hydroxy-gon-5-ene-3,17-dione have lead to the unequivocal assignment of the 10alpha stereochemistry to C10, showing that an inversion of configuration occurred during formation of the 3,17-diketal. From the Swern oxidation of this compound, 11alpha-(methylthio)methoxy-10alpha-gonene was obtained as the major product instead of the desired 11-ketone. Modeling studies showed that the configurational instability at C10 is determined by the presence of the 11alpha-hydroxyl group. |
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Keywords: | Crystal structures 10α-Steroids Ketalization Desogestrel Swern oxidation |
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