A NEW STRATEGY FOR THE PREPARATION OF 11-OXYGENATED STEROIDS SYNTHESIS OF (+ -)-ADRENOSTERONE/

Authors
GRIECO PA MAY SA KAUFMAN MD
Citation
Pa. Grieco et al., A NEW STRATEGY FOR THE PREPARATION OF 11-OXYGENATED STEROIDS SYNTHESIS OF (+ -)-ADRENOSTERONE/, Tetrahedron letters, 39(39), 1998, pp. 7047-7050
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
39
Year of publication
1998
Pages
7047 - 7050
Database
ISI
SICI code
0040-4039(1998)39:39<7047:ANSFTP>2.0.ZU;2-V
Abstract
Conjugate 1,4-addition of butyldimethylsilyl)oxy]-2methyl-1,3-cyclohex adiene (5) to 2-methylcyclopentenone in highly polar media and subsequ ent alkylation of the resultant silyl enol ether (4) with phenylthiodi enyl carbonate 10 in 5.0 M LiClO4. Et2O provides substrate 2. Exposure of 2 to TMSOTf/ TMSOCH2CH2OTMS affords tetracyclic bis-ketal 3, which is converted into (+/-)-adrenosterone (1) in four steps. (C) 1998 Els evier Science Ltd. All rights reserved.