ACID-CATALYZED REARRANGEMENT AND ACYL MIGRATION STUDIES ON 9-DIHYDRO-13-ACETYLBACCATIN-III, A MAJOR TAXANE FROM TAXUS-CANADENSIS

Authors
ZAMIR LO BALACHANDRAN S ZHENG YF NEDEA ME CARON G NIKOLAKAKIS A VISHWAKARMA RA SAURIOL F MAMER O
Citation
Lo. Zamir et al., ACID-CATALYZED REARRANGEMENT AND ACYL MIGRATION STUDIES ON 9-DIHYDRO-13-ACETYLBACCATIN-III, A MAJOR TAXANE FROM TAXUS-CANADENSIS, Tetrahedron, 53(47), 1997, pp. 15991-16008
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
47
Year of publication
1997
Pages
15991 - 16008
Database
ISI
SICI code
0040-4020(1997)53:47<15991:ARAAMS>2.0.ZU;2-B
Abstract
A detailed investigation of the rearrangement of the major taxane from Taxus canadensis enables to suggest the sequence of the reactions inv olved: 9-dihydro-13-acetylbaccatin III - abeo-taxanes with intact oxet ane and acyl migration - abeo-taxanes with intact oxetane and deacylat ion - abeo-taxanes with opening of the oxetane and various acyl migrat ions including two unusual benzoyl shifts. (C) 1997 Elsevier Science L td.