E. Modica, G. Bombieri, D. Colombo
Aug 1, 2003
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0
Influential Citations
29
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Journal
European Journal of Organic Chemistry
Abstract
Four new estrone derivatives were isolated after treatment of estrone 3-methyl ether (3-methoxyestra-1,3,5(10)-trien-17-one (3) with tert-butyl hydroperoxide and cobalt acetate. Three of the four steroidal compounds − the 9α-(tert-butylperoxy)-6-one 4, the 9α-hydroxy-6-one 5, and the 9β-hydroxy-6-one 7 − originated from oxidation at the 6- and 9-positions. In contrast, oxidation of 3 to a 9β-(tert-butylperoxy) compound afforded the 8-hydroxy-9-cyclodecanone derivative 6 through a molecular rearrangement involving the cleavage of the 8−9 bond. The structures of the compounds were secured by spectroscopic evidence including COSY, HSQC, and NOESY experiments combined with X-ray crystallographic analysis and molecular modeling studies. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)