SYNTHESIS OF STEREOISOMERIC DIMETHYL 4,7- EPOXY-HYDROAZULENE-5,6-DICARBOXYLATES WITH THE LACTARANE SKELETON

Authors
TOCHTERMANN W BRUHN S MEINTS M WOLFF C PETERS EM PETERS K VONSCHNERING HG
Citation
W. Tochtermann et al., SYNTHESIS OF STEREOISOMERIC DIMETHYL 4,7- EPOXY-HYDROAZULENE-5,6-DICARBOXYLATES WITH THE LACTARANE SKELETON, Tetrahedron, 51(6), 1995, pp. 1623-1630
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
6
Year of publication
1995
Pages
1623 - 1630
Database
ISI
SICI code
0040-4020(1995)51:6<1623:SOSD4E>2.0.ZU;2-3
Abstract
Methylenation of the keto group of the cis-diester 1 by Wittig reactio n gives under inversion on C-6 the trans-diester 2. The revised stereo chemistry of 2 was established by crystal structure analysis of the hy drogenation product 3 and by comparison of NMR data. On the other hand methylenation of 1 with the Nysted reagent leads to the cis-diester 5 which is hydrogenated to the trimethylhydroazulene 6.