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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

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  • 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.

Abstract

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Doubling up: The direct bio-inspired dimerization of commercially available amine-free tryptophan derivatives in aqueous acidic media provides C2-symmetrical and nonsymmetrical dimeric compounds. Further processing completes the concise syntheses of naturally occurring dimeric diketopiperazine alkaloids such as (+)-WIN 64821 (see picture) in overall yields of up to 20 %.

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