A novel base-promoted rearrangement of eudesmanolide sesquiterpenoid to the salvialane sesquiterpene

Authors
Xia, WJ Tu, YQ Li, DR
Citation
Wj. Xia et al., A novel base-promoted rearrangement of eudesmanolide sesquiterpenoid to the salvialane sesquiterpene, SYN COMMUN, 31(10), 2001, pp. 1613-1617
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
10
Year of publication
2001
Pages
1613 - 1617
Database
ISI
SICI code
0039-7911(2001)31:10<1613:ANBROE>2.0.ZU;2-R
Abstract
An eudesmanolide sesquiterpene epoxide has been transformed to an alpha -hy droxy ketone with the salviane sesquiterpene skeleton through a novel carbo n-carbon rearrangement promoted by excess of NaOMe in Et2O at room temperat ure which accomplished the first synthesis of the salviane kind of sesquite rpene skeleton. A possible reaction mechanism is also discussed.