SYNTHESIS OF FUNCTIONALIZED HYDROAZULENES - A NEW APPROACH TO THE LACTARANE SKELETON

Authors
TOCHTERMANN W BRUHN S MEINTS M WOLFF C
Citation
W. Tochtermann et al., SYNTHESIS OF FUNCTIONALIZED HYDROAZULENES - A NEW APPROACH TO THE LACTARANE SKELETON, Tetrahedron, 50(32), 1994, pp. 9657-9670
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
32
Year of publication
1994
Pages
9657 - 9670
Database
ISI
SICI code
0040-4020(1994)50:32<9657:SOFH-A>2.0.ZU;2-E
Abstract
An efficient regioselective and stereoselective approach to the hydroa zulenic skeleton of the lactarane sesquiterpenes is described. The fur an 1 is transformed to the key intermediate 4. Regioselective intramol ecular aldol reaction of 4 leads to the hydroazulenone 5 in excellent yield. Catalytic hydrogenation, followed by Wittig reaction, gives the compound 8, which is converted to the trimethylhydroazulenes 9 and 10 with five and seven stereogenic centers, respectively.