期刊
TETRAHEDRON LETTERS
卷 49, 期 39, 页码 5614-5617出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.07.042
关键词
steroids; estrone; 5 alpha-androstane; dioxiranes; methyl(trifluoromethyl)dioxirane; hydroxylation; regioselectivity
资金
- Italian Ministry of University and of Scientific Research
- CNR (Italy)
- Cambridge Crystallographic Data Centre, (12 Union Road), Cambridge, C132 1EZ, UK [691166, 691164, 691165, 691167]
Using methyl](trifluoromethyl)dioxirane (1b), 3 beta,6 alpha,17 beta-triacetoxy-5 alpha-androstane (6) could be selectively transformed into its C-14 hydroxy derivative (7) and into the valuable C-12 ketone steroid (8). in high yields under mild reaction conditions. Similarly, the oxidation of 3 alpha-estrone acetate (4) with 1b was carried Out to yield selectively the steroid C-9 hydroxy derivative (5). The high regio- and site-selectivity attained demonstrates that the powerful dioxirane 1b is the reagent of choice to synthesize valuable oxyfunctionalized steroid derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
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