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- Title
Bio-Inspired Dimerization Reaction of Tryptophan Derivatives in Aqueous Acidic Media: Three-Step Syntheses of (+)-WIN 64821, (−)-Ditryptophenaline, and (+)-Naseseazine B.
- Authors
Tadano, Shinji; Mukaeda, Yuri; Ishikawa, Hayato
- Abstract
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 %.
- Subjects
DIMERIZATION; CHEMICAL reactions; BIOSYNTHESIS; DIKETOPIPERAZINES; TRYPTOPHAN derivatives; AQUEOUS solutions; PEPTIDE derivatives
- Publication
Angewandte Chemie International Edition, 2013, Vol 52, Issue 31, p7990
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201303143