Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin.
A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon. [structure: see text]
Kobayashi
Shoji
S
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Alizadeh
Babak H
BH
Sasaki
Shin-ya
SY
Oguri
Hiroki
H
Hirama
Masahiro
M
D000818:Animals; D002922:Ciguatoxins / Q000138:chemical synthesis*; D004141:Dinoflagellida / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis; D015394:Molecular Structure
D006576:Heterocyclic Compounds, 4 or More Rings; D002922:Ciguatoxins