TETRACYCLIC TRITERPENES .15. RING EXPANSION OF STEROIDAL ACYLOINS - YDROXY-14-ALPHA-METHYL-4-NOR-5-ALPHA-CHOLEST-8-ENE AND HYDROXY-14-ALPHA-METHYL-4-NOR-5-BETA-CHOLEST-8-ENE

Authors
PARYZEK Z MARTYNOW J
Citation
Z. Paryzek et J. Martynow, TETRACYCLIC TRITERPENES .15. RING EXPANSION OF STEROIDAL ACYLOINS - YDROXY-14-ALPHA-METHYL-4-NOR-5-ALPHA-CHOLEST-8-ENE AND HYDROXY-14-ALPHA-METHYL-4-NOR-5-BETA-CHOLEST-8-ENE, Journal of the Chemical Society. Perkin transactions. I, (20), 1994, pp. 3047-3050
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
20
Year of publication
1994
Pages
3047 - 3050
Database
ISI
SICI code
0300-922X(1994):20<3047:TT.REO>2.0.ZU;2-W
Abstract
The base- and acid-catalysed ring A expansion of steroidal acyloins, 3 -acetyl-3-hydroxy-14 alpha-methyl-4-nor-5 alpha- and -5 beta-cholest-8 -ene, gave 3,14-dimethyl-4-oxo-5 alpha- and -5 beta-cholestane derivat ives. The regioselective migration of the secondary carbon atom C-3 is explained by the steric factors and conformational preference for the formation of the chair-like transition state.