THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .24. ACID AND BASE-CATALYZED REARRANGEMENTS OF 9,10-DIOXOTAXANES

Authors
APPENDINO G JAKUPOVIC J VARESE M BOMBARDELLI E
Citation
G. Appendino et al., THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .24. ACID AND BASE-CATALYZED REARRANGEMENTS OF 9,10-DIOXOTAXANES, Tetrahedron letters, 37(5), 1996, pp. 727-730
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
5
Year of publication
1996
Pages
727 - 730
Database
ISI
SICI code
0040-4039(1996)37:5<727:TCAOOT>2.0.ZU;2-A
Abstract
Treatment of 10-dehydro-10-deacetylbaccatin III (2a) with trichloroace tic acid gave the bis-abeotaxane 3, whereas treatment of 2a and its 7- epimer (2b) with bases (DBU, NaH) triggered a tandem retroaldol-Michae l reaction, giving a compound of the 7,8-seco-8,12-cyclotaxane type. B oth skeletal rearrangements were accompanied by extensive reorganisati on of the oxygen functions in the southern hemisphere of the molecule.