TY - JOUR
T1 - A concise route to two distinct E-ring structures of ciguatoxins
AU - Inoue, Masayuki
AU - Iwatsu, Masafumi
AU - Yamashita, Shuji
AU - Hirama, Masahiro
PY - 2007/4/13
Y1 - 2007/4/13
N2 - Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of different ring sizes, found in ciguatoxins.From the common oxepane intermediate, the seven-membered E-ring was prepared in three steps, and the eight-membered E-ring was synthesized in seven steps using ring expansion and olefin isomerization as key reactions.
AB - Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of different ring sizes, found in ciguatoxins.From the common oxepane intermediate, the seven-membered E-ring was prepared in three steps, and the eight-membered E-ring was synthesized in seven steps using ring expansion and olefin isomerization as key reactions.
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U2 - 10.3987/COM-06-S(K)16
DO - 10.3987/COM-06-S(K)16
M3 - Article
AN - SCOPUS:34547840165
VL - 72
SP - 327
EP - 338
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
ER -