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

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

Herein, we report a practical synthesis of 2-D-l-tryptophan via sequential Ir-catalyzed CH 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. H...

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Bibliographic Details
Published in:Tetrahedron Vol. 75; no. 15; pp. 2261 - 2264
Main Authors: Vallakati, Ravikrishna, Plotnikov, Abel T., Altman, Ryan A.
Format: Journal Article
Language:English
Published: England Elsevier Ltd 12-04-2019
Subjects:
C[sbnd]H borylation
Deborylative deuteration
Deuterium labeling
L-tryptophan
Metal-catalysis
Deuterium labeling
Metal-catalysis
CH borylation
L-tryptophan
Deborylative deuteration
L-Tryptophan
C–H Borylation
Metal-Catalysis
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Summary:Herein, we report a practical synthesis of 2-D-l-tryptophan via sequential Ir-catalyzed CH 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. [Display omitted]
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.02.054