X-ray crystallographic studies performed on the product of the ketalization reaction of 13β-ethyl-11α-hydroxy-gon-5-ene-3,17-dione have lead to the unequivocal assignment of the 10α stereochemistry to C10, showing that an inversion of configuration occurred during formation of the 3,17-diketal. From the Swern oxidation of this compound, 11α-(methylthio)methoxy- 10α-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 11α-hydroxyl group.

Crystal structures of 10alpha-gon-5-enes from the synthetic pathway to desogestrel / E. Modica, D. Colombo, F. Ronchetti, A. Scala, G. Bombieri, N. Marchini, L. Toma. - In: STEROIDS. - ISSN 0039-128X. - 70:9(2005), pp. 660-666. [10.1016/j.steroids.2005.03.006]

Crystal structures of 10alpha-gon-5-enes from the synthetic pathway to desogestrel

E. Modica
Primo
;
D. Colombo
Secondo
;
F. Ronchetti;G. Bombieri;
2005

Abstract

X-ray crystallographic studies performed on the product of the ketalization reaction of 13β-ethyl-11α-hydroxy-gon-5-ene-3,17-dione have lead to the unequivocal assignment of the 10α stereochemistry to C10, showing that an inversion of configuration occurred during formation of the 3,17-diketal. From the Swern oxidation of this compound, 11α-(methylthio)methoxy- 10α-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 11α-hydroxyl group.
Settore CHIM/08 - Chimica Farmaceutica
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/5560
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