Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione

Authors
Soldermann, N Velker, J Vallat, O Stoeckli-Evans, H Neier, R
Citation
N. Soldermann et al., Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione, HELV CHIM A, 83(9), 2000, pp. 2266-2276
Citations number
67
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
83
Issue
9
Year of publication
2000
Pages
2266 - 2276
Database
ISI
SICI code
0018-019X(2000)83:9<2266:AOTNTP>2.0.ZU;2-J
Abstract
The novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement shows a high diastereoselectivity for the Ireland-Claisen rearrangement st arting from the endo-product of the Diels-Alder reaction. Based on this mec hanistic knowledge, the novel tandem process could be applied to the synthe sis of rac-juvabione.