TY - JOUR
T1 - Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C
AU - Uehara, Hisatoshi
AU - Oishi, Tohru
AU - Inoue, Masayuki
AU - Shoji, Mitsuru
AU - Nagumo, Yoko
AU - Kosaka, Masashi
AU - Le Brazidec, Jean Yves
AU - Hirama, Masahiro
PY - 2002/8/5
Y1 - 2002/8/5
N2 - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.
AB - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.
KW - CTX3C
KW - Ciguatoxin
KW - Intramolecular carbonyl olefination
KW - Low-valent titanium complex
KW - Polyether
KW - Ring-closing metathesis
UR - http://www.scopus.com/inward/record.url?scp=0037026010&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037026010&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)00660-9
DO - 10.1016/S0040-4020(02)00660-9
M3 - Article
AN - SCOPUS:0037026010
SN - 0040-4020
VL - 58
SP - 6493
EP - 6512
JO - Tetrahedron
JF - Tetrahedron
IS - 32
ER -