Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin

Shoji Kobayashi; Babak H Alizadeh; Shin-ya Sasaki; Hiroki Oguri; Masahiro Hirama

doi:10.1021/ol0364475

Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin

Org Lett. 2004 Mar 4;6(5):751-4. doi: 10.1021/ol0364475.

Authors

Shoji Kobayashi¹, Babak H Alizadeh, Shin-ya Sasaki, Hiroki Oguri, Masahiro Hirama

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.

PMID: 14986966
DOI: 10.1021/ol0364475

Abstract

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]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Ciguatoxins / chemical synthesis*
Dinoflagellida / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Molecular Structure

Substances

Heterocyclic Compounds, 4 or More Rings
Ciguatoxins