Practical one-pot conversion of 17beta-estradiol to 10beta-hydroxy- (p-quinol) and 10beta-chloro-17beta-hydroxyestra-1,4-dien-3-one |
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| Authors: | Lista Liliana Manini Paola Napolitano Alessandra Pezzella Alessandro d'Ischia Marco |
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| Affiliation: | Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Italy. |
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| Abstract: | An efficient one-pot procedure for the preparation of 10beta,17beta-dihydroxyestra-1,4-dien-3-one (p-quinol, 1, 75%) is reported, involving oxidation of 17beta-estradiol with potassium permanganate. Similar treatment of 17beta-estradiol with sodium chlorite led to 10beta-chloro-17beta-hydroxyestra-1,4-dien-3-one (2) in 44% yield along with smaller amounts 4-chloro-10beta,17beta-dihydroxyestra-1,4-dien-3-one (3), 2,10beta-dichloro-17beta-hydroxyestra-1,4-dien-3-one (4), and 4,10beta-dichloro-17beta-hydroxyestra-1,4-dien-3-one (5). |
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| Keywords: | NMR, nuclear magnetic resonance COSY, 1H,1H Correlation spectroscopy DQF-COSY, double quantum filtered correlation spectroscopy HMQC, 1H,13C heteronuclear multiple quantum coherence HMBC, 1H,13C heteronuclear multiple bond correlation ROESY, rotating Overhauser effect spectroscopy ESIMS, electrospray ionization mass spectrometry HRESI, high resolution electrospray ionization TLC, thin layer chromatography CD, circular dichroism |
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