O
N
N
N
O
O
Janoxepin
Strychnine
O
N
CO 2 H
Olopatadine
Aphanamixoid A
N
O
AcO
N
O
O
O
OAc
S S
Acetylaranotin
O
OAc
O
O
O
N
O
H
N
H
O
H
O
HO
OH
O
Artocarpol D
O
Cl
H
Br
H
(+)-Rogioloxepane
O
Cl
O
Pterulone
(antiplasmodial)
(antifeedent activity)
(antihistaminic drug)
(antiproliferative activity)
(antiinflammatory properties)
(antifungal activity)
(poison)
Fig. 1 Oxepins, benzoxepines, oxepenes and related structures
O
O
O
O
O
OH
OH
Brevenal
O
O
O
OH
H
OH
OHC
H
H
O
O
O
OH
H
H
H
H
(-)-Brevisin
OH
O
O
O
O
O
O
O
O
HO Me Me H
H
H
H
H
H
H
H
H Me
Me
H
OH
OH
H
Gambierol
(marine toxin)
O
C 3 H 7
C 6 H 13
(+)-Isolaurepan
H
H
H
H
OHC
H
H
H
O
OH
HO
O
Zoapatanol
(antifertility activity)
O
HO
O
O
H
HO
Punctaporonin
CO 2 H
(marine toxin)
(marine toxin)
Fig. 2 Natural-occurring oxepanes and polycyclic ethers
Synthesis of Seven-Membered Ring Ethers and Lactones
285