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Bio-Inspired Dimerization Reaction of Tryptophan Derivatives in Aqueous Acidic Media: Three-Step Syntheses of (+)-WIN 64821, (−)-Ditryptophenaline, and (+)-Naseseazine B


  • This work was supported financially by a Grant-in-Aid for Scientific Research (B) (25288050) and Exploratory Research (25670005) from JSPS, a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysis” (No. 2304) (24105528) from MEXT, the Naito Foundation, the Uehara Memorial Foundation, the NOVARTIS Foundation (Japan) for the promotion of Science, a SUNBOR Grant from the Suntory Institute for Bioorganic Research, and the JGC-S Scholarship Foundation. We also thank Prof. Hiroshi Nishino (Kumamoto University), Prof. Ryo Irie (Kumamoto University), and Prof. Hiromitsu Takayama (Chiba University) for their support and guidance.


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Gedoppelt: Die direkte bioinspirierte Dimerisierung kommerziell erhältlicher aminfreier Tryptophanderivate in saurem wässrigem Medium liefert C2-symmetrische und nichtsymmetrische dimere Verbindungen. Weitere Reaktionen schließen knappe Synthesen natürlich vorkommender dimerer Diketopiperazinalkaloide wie (+)-WIN 64821 (siehe Bild) in Gesamtausbeuten bis 20 % ab.

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