Unusual boron trifluoride-catalyzed reactions of taxinine derivatives withalpha- and beta-4(20)-epoxides

Authors
Hosoyama, H Shigemori, H Kobayashi, J
Citation
H. Hosoyama et al., Unusual boron trifluoride-catalyzed reactions of taxinine derivatives withalpha- and beta-4(20)-epoxides, TETRAHEDR L, 40(11), 1999, pp. 2149-2152
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
11
Year of publication
1999
Pages
2149 - 2152
Database
ISI
SICI code
0040-4039(19990312)40:11<2149:UBTROT>2.0.ZU;2-S
Abstract
Boron trifluoride-catalyzed reaction of beta-4(20)-epoxy-5-O-triethylsilylt axinine A (1) gave the 3,5-diene (3) and the 3,8-cyclopropane (4) derivativ es, while the similar reaction of the corresponding alpha-4(20)-epoxide (2) afforded the ring contracted derivative (5) and its hemiacetal dimer (6). Plausible mechanisms of these reactions containing 1,2-hydride shift (3 and 4 from 1) or pinacol-type rearrangement (5 and 6 from 2) are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.