EFFICIENT SYNTHESIS OF THE TAXANE C-RING BY FRAGMENTATION REACTION OFA BICYCLO[2.2.2]OCTANE DERIVATIVE

Authors
HIRAI Y SUGA T NAGAOKA H
Citation
Y. Hirai et al., EFFICIENT SYNTHESIS OF THE TAXANE C-RING BY FRAGMENTATION REACTION OFA BICYCLO[2.2.2]OCTANE DERIVATIVE, Tetrahedron letters, 38(28), 1997, pp. 4997-5000
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
28
Year of publication
1997
Pages
4997 - 5000
Database
ISI
SICI code
0040-4039(1997)38:28<4997:ESOTTC>2.0.ZU;2-6
Abstract
Compounds 3, the C/D ring moiety of paclitaxel without a 7-hydroxyl gr oup, and 4, the C ring moiety of O-cinnamoyltaxicin-I (2), were synthe sized stereoselectively from methyl S)-3-(2,2-dimethyl-1,3-dioxolan-4- yl)-2-pentenoate (5) using the fragmentation reaction of bicyclo[2.2.2 ]-octane derivative 9 as a key step to give 10. (C) 1997 Elsevier Scie nce Ltd.