Total Synthesis of (−)-5,6,11-Trideoxytetrodotoxin and Its 4-Epimer

Total Synthesis of (−)-5,6,11-Trideoxytetrodotoxin and Its 4-Epimer

The first total synthesis of 5,6,11-trideoxytetrodotoxin (1) and its 4-epimer were achieved. The synthesis is characterized by the stereoselective construction of the quaternary amino carbon center at C8a by an asymmetric transferring Strecker synthesis and the highly efficient conversion of cyanohy...

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Veröffentlicht in:Organic letters 2006-10, Vol.8 (21), p.4971-4974
Hauptverfasser: Umezawa, Taiki, Hayashi, Toshihiro, Sakai, Hiroshi, Teramoto, Hidetoshi, Yoshikawa, Takeshi, Izumida, Masashi, Tamatani, Yoshinori, Hirose, Tadashi, Ohfune, Yasufumi, Shinada, Tetsuro
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Structure
Nitriles - chemistry
Stereoisomerism
Tetrodotoxin - analogs & derivatives
Tetrodotoxin - chemical synthesis
Tetrodotoxin - chemistry
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Zusammenfassung:The first total synthesis of 5,6,11-trideoxytetrodotoxin (1) and its 4-epimer were achieved. The synthesis is characterized by the stereoselective construction of the quaternary amino carbon center at C8a by an asymmetric transferring Strecker synthesis and the highly efficient conversion of cyanohydrin 4 to 1 via intramolecular cyclization reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062098d