Progress towards an intramolecular Diels-Alder ring-expansion approach to taxinine: the interplay of Lewis acids and high pressure

Authors
Phillips, AJ Morris, JC Abell, AD
Citation
Aj. Phillips et al., Progress towards an intramolecular Diels-Alder ring-expansion approach to taxinine: the interplay of Lewis acids and high pressure, TETRAHEDR L, 41(15), 2000, pp. 2723-2727
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
15
Year of publication
2000
Pages
2723 - 2727
Database
ISI
SICI code
0040-4039(20000408)41:15<2723:PTAIDR>2.0.ZU;2-3
Abstract
A concise route to a bicyclo[4.2.1] ring system, based on an intramolecular Diels-Alder reaction, has been developed. Preliminary results on the inter play between Lewis acids and high pressure to facilitate the reaction are d escribed. Products with isomerized double bonds were obtained with 1 equiva lent of Lewis acid at 0 degrees C. The stereochemistry of these compounds h as been determined by X-ray crystallography. Double bond isomerization is s uppressed by the use of excess Lewis acid at -78 degrees C or high pressure . (C) 2000 Elsevier Science Ltd. All rights reserved.