214
5.6 Synthesis of Eremoligenol and Eremophilone
An intramolecular Diels-Alder route to the title compounds, starting from tetraene
1087, was developed by Näf et al. This afforded the bicyclic enone 1088 (Scheme 8)
[320], which was transformed to eremophilone (1091) through enone 1089. The
enone 1089 was also converted to eremoligenol (14) via 1090.
OPP
H
A H
H
H
1
OH
HO
1095 (5-epiaristrochene)
1092 ((E,E )-farnesyl
diphosphate)
1093
1094
1096 (capsidiol)
1097
1098
1099
1100
Scheme 9 Synthesis scheme for eremophiladienes 1095, 1097–1100, and 1 by Coates’ group
CO 2 Et
O
CO 2 Et
O
CO 2 Et
CO 2 Et
OH
14 (eremoligenol)
O
1091 (eremophilone)
1087
1088
1089
1090
Scheme 8 Synthesis scheme of eremoligenol (14) and eremophilone (1091) by Näf et al.
5.7 Synthesis of Eremophiladienes
Coates’ group prepared six eremophiladiene isomers (1, 1095, and 1097–1100)
from capsidiol (1096), obtained by elicitation from green peppers (Scheme 9)
[321]. 5-Epiaristrochene (1095) was also obtained from the incubation of
M. Tori and C. Kuroda