Convergent synthesis of the right-hand segment of ciguatoxin.
[reaction: see text] A convergent synthesis of the right-hand half of ciguatoxin (the HIJKLM ring system) has been achieved with complete stereocontrol in the introduction of the stereocenters on the eight-membered I ring. Key steps are Sonogashira coupling, dicobalt complexation, intramolecular conjugate addition, and hydrogenation of an endo-olefin to provide the 39-alpha-methyl group.
Hamajima
Akinari
A
Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Isobe
Minoru
M
D036841:Ciguatera Poisoning; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006865:Hydrogenation; D008967:Molecular Biology; D015394:Molecular Structure
D002922:Ciguatoxins