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Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

✍ Scribed by Wei Wang; Chiyi Xiong; Jianqing Yang; Victor J Hruby

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
60 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of a-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D-and L-a-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.

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