Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions

TETRAHEDRON

卷:75

Article

Vallakati, Ravikrishna¹  Plotnikov, Abel T.¹  Altman, Ryan A.¹ 

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

关键词: L-tryptophan;    C-H borylation;    Deborylative deuteration;    Metal-catalysis;    Deuterium labeling;   

DOI  :  10.1016/j.tet.2019.02.054

来源: Elsevier

【 摘 要 】

Herein, we report a practical synthesis of 2-D-c-tryptophan via sequential Ir-catalyzed C-H borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc and methyl ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D-L-Tryptophan is stable in many buffers used for biological studies. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free