TETRACYCLIC TRITERPENES .16. SYNTHESIS OF 31-NORCUCURBITANE AND FUSIDANE DERIVATIVES IN THE SKELETAL REARRANGEMENTS OF 9,11-EPOXY-4-BETA-DEMETHYL-5-ALPHA-LANOSTANES

Authors
PARYZEK Z MARTYNOW J
Citation
Z. Paryzek et J. Martynow, TETRACYCLIC TRITERPENES .16. SYNTHESIS OF 31-NORCUCURBITANE AND FUSIDANE DERIVATIVES IN THE SKELETAL REARRANGEMENTS OF 9,11-EPOXY-4-BETA-DEMETHYL-5-ALPHA-LANOSTANES, Journal of the Chemical Society. Perkin transactions. I, (2), 1996, pp. 201-207
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
2
Year of publication
1996
Pages
201 - 207
Database
ISI
SICI code
0300-922X(1996):2<201:TT.SO3>2.0.ZU;2-T
Abstract
The BF3 . Et(2)O-catalysed rearrangement of 9 beta,11 beta-epoxy-4 bet a-demethyl-5 alpha-lanostan-7-one derivatives 11 and 12 in acetic anhy dride resulted in formation of 19(10-->9 beta)abeo compounds (31-norcu curbitanes) 20-22 or 23 and 24, respectively. The extent of a rearrang ement was dependent on the substituent at position 3 of the steroid. R eaction of the 9 alpha,11 alpha-epoxide 17 under similar conditions ga ve fusidenone 25 (31-norprotostane) in high yield which had the carbon skeleton characteristic of the steroidal antibiotic, fusidic acid.