A novel rearrangement of eudesmanolide enol ester epoxide: facile 1-step construction of the salvialane sesquiterpene skeleton

Authors
Wu, JX De, RL Lei, S Tu, YQ
Citation
Jx. Wu et al., A novel rearrangement of eudesmanolide enol ester epoxide: facile 1-step construction of the salvialane sesquiterpene skeleton, TETRAHEDR-A, 12(10), 2001, pp. 1459-1462
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
10
Year of publication
2001
Pages
1459 - 1462
Database
ISI
SICI code
0957-4166(20010622)12:10<1459:ANROEE>2.0.ZU;2-4
Abstract
A Nobel carbon-carbon rearrangement for the eudesmanolide sesquiterpene eno l ester epoxide in the presence of a catalytic amount of Lewis acids (3 - 1 0 mol%) or an excess of NaOMe is disclosed. This reaction,vas developed to give a facile. one-step procedure for the construction of naturally occurri ng and bioactive salvialane sesquiterpenes. The reaction conditions were in vestigated extensively and a possible reaction mechanism is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.