Convergent Synthesis of the Right-Hand Segment of Ciguatoxin

Convergent Synthesis of the Right-Hand Segment of Ciguatoxin

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...

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Veröffentlicht in:Organic letters 2006-03, Vol.8 (6), p.1205-1208
Hauptverfasser: Hamajima, Akinari, Isobe, Minoru
Format: Artikel
Sprache:eng
Schlagworte:
Ciguatera Poisoning
Ciguatoxins - chemical synthesis
Ciguatoxins - chemistry
Cyclization
Hydrogenation
Molecular Biology
Molecular Structure
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Zusammenfassung: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-α-methyl group.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0600741