SIMPLE SYNTHETIC APPROACH TO 6-OXA STEROIDS - SYNTHESIS OF 6-OXA-5-BETA-PREGNANE-3,20-DIONE

Authors
NICOLETTI D GHINI AA BRACHETCOTA AL BURTON G
Citation
D. Nicoletti et al., SIMPLE SYNTHETIC APPROACH TO 6-OXA STEROIDS - SYNTHESIS OF 6-OXA-5-BETA-PREGNANE-3,20-DIONE, Journal of the Chemical Society. Perkin transactions. I, (9), 1995, pp. 1089-1093
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
9
Year of publication
1995
Pages
1089 - 1093
Database
ISI
SICI code
0300-922X(1995):9<1089:SSAT6S>2.0.ZU;2-J
Abstract
A two-step synthesis of 19-functionalized 6-oxapregnanes from a 5 alph a,6 beta-dihydroxypregnane is described. Deoxygenation at C-19 afforde d a 6-oxapregnane, which was converted into 6-oxa-5 beta-pregnane-3,20 -dione 7. An insight into the mechanism of formation of the key interm ediate, a 5,6-secosteroid, via a hypoiodite type reaction is also give n.