Tetrahedron

Synthesis of tricyclopentanoid sesquiterpenes via rearrangement routes:(±)-modhephene,(±)-epimodhephene and (±)-isocomene

L Fitjer, M Majewski, H Monzó-Oltra

Index: Fitjer, Lutz; Majewski, Marita; Monzo-Oltra, Honorato Tetrahedron, 1995 , vol. 51, # 32 p. 8835 - 8852

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Citation Number: 33

Abstract

Based on model studies with dispiroundecane 10, dispiroundecane 1 has been synthesized and rearranged to (±)-modhephene 6 and (±)-isocomene 7. The epimeric dispiroundecane 9 yields (±)-epimodhephene 12. A total of thirteen rearrangement products (6, 7, 12, 37, 38, 39, 42, 43, 44, 55, 57, 64, 67) have been isolated from 1 and/or 9, including six unnatural triquinanes. Two of these (55, 57) are formed by unusual 1, 3-and 1, 4-shifts, respectively. ...