POLYSPIRANES .25. CASCADE REARRANGEMENTS .20. SYNTHESIS OF TRICYCLOPENTANOID SESQUITERPENES VIA REARRANGEMENT ROUTES - (+ -)-MODHEPHENE, (+/-)-EPIMODHEPHENE AND (+/-)-ISOCOMENE/

Authors
FITJER L MAJEWSKI M MONZOOLTRA H
Citation
L. Fitjer et al., POLYSPIRANES .25. CASCADE REARRANGEMENTS .20. SYNTHESIS OF TRICYCLOPENTANOID SESQUITERPENES VIA REARRANGEMENT ROUTES - (+ -)-MODHEPHENE, (+/-)-EPIMODHEPHENE AND (+/-)-ISOCOMENE/, Tetrahedron, 51(32), 1995, pp. 8835-8852
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
32
Year of publication
1995
Pages
8835 - 8852
Database
ISI
SICI code
0040-4020(1995)51:32<8835:P.CR.S>2.0.ZU;2-G
Abstract
Based on model studies with dispiroundecane 10, dispiroundecane 1 has been synthesized and rearranged to (+/-)-modhephene 6 and (+/-)-isocom ene 7. The epimeric dispiroundecane 9 yields (+/-)-epimodhephene 12. A total of thirteen rearrangement products (6, 7, 12, 37, 38, 39, 42, 4 3, 44, 55, 57, 64, 67) have been isolated from 1 and/or 9, including s ix unnatural triquinanes. Two of these (55, 57) are formed by unusual 1,3- and 1,4-shifts, respectively. A mechanistic rationale on the basi s of force field calculations is given.