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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
Author(s) -
Tadano Shinji,
Mukaeda Yuri,
Ishikawa Hayato
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303143
Subject(s) - aqueous medium , amine gas treating , combinatorial chemistry , tryptophan , chemistry , computer science , aqueous solution , organic chemistry , amino acid , biochemistry
Doubling up : The direct bio‐inspired dimerization of commercially available amine‐free tryptophan derivatives in aqueous acidic media provides C 2 ‐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 %.