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 inTetrahedron Vol. 75; no. 15; pp. 2261 - 2264
Main Authors Vallakati, Ravikrishna, Plotnikov, Abel T., Altman, Ryan A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 12.04.2019
Elsevier
Subjects
C[sbnd]H borylation
Chemistry
Chemistry, Organic
Deborylative deuteration
Deuterium labeling
L-tryptophan
Metal-catalysis
Physical Sciences
Science & Technology
Deuterium labeling
Metal-catalysis
CH borylation
L-tryptophan
Deborylative deuteration
SELECTIVE DEUTERATION
TRYPTOPHAN
C-H borylation
ARENES
MILD
FUNCTIONALIZATION
HETEROARENES
METABOLISM
BIS(PINACOLATO)DIBORON
HYDROGEN-DEUTERIUM EXCHANGE
BORYLATION
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]
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.02.054