The Construction of the A,B,C-ring System of Ciguatoxin

✍ Scribed by Takahiro Oka; Kenshu Fujiwara; Akio Murai

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 619 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10107-1

✦ Synopsis

A&mrcc The first consrmctionof theA,B,C-ringsystemhavingall of the naturataubstituenta in ciguatoxin wasachievedfromB-glucose. O 1997EkevierScienceLtd. Ciguatoxitt 1 was isolated as the principal toxin causing ciguatera from moray eel Garnno thorax javanicur.The structureof 1 determined by Yasumoto et al. has a characteristicpolycyclicsystemincluding Reagentsand Conditions: a) Eu(fod&(3.0 q), toluene,80 'C, 15h (38%);b) CltX#O#l, pyridine, DMAP, C~~, r.t., 2 h (20, 60%; 21, 34%); c) DBU, toluene, nXlux, 1 h (88%); d) Na+[PhSeB(OEt&]-, EtOH, influx, 3 h (62%);e) ~02, pyridine,C~~, O"C+r.t., 1h (~59%; 23, 39%).