Literature DB >> 31130755

Synthesis of 2-D-L-Tryptophan by Sequential Ir-Catalyzed Reactions.

Ravikrishna Vallakati1, Abel T Plotnikov1, Ryan A Altman1.   

Abstract

Herein, we report a practical synthesis of 2-D-L-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.

Entities:  

Keywords:  C–H Borylation; Deborylative deuteration; Deuterium labeling; L-Tryptophan; Metal-Catalysis

Year:  2019        PMID： 31130755      PMCID： PMC6532784          DOI： 10.1016/j.tet.2019.02.054

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  31 in total

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Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2002-11       Impact factor: 60.622

2.  Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: nitrogen-directed aromatic borylation.

Authors:  Sulagna Paul; Ghayoor A Chotana; Daniel Holmes; Rebecca C Reichle; Robert E Maleczka; Milton R Smith
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

Review 3.  The renaissance of H/D exchange.

Authors:  Jens Atzrodt; Volker Derdau; Thorsten Fey; Jochen Zimmermann
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4.  Asymmetric synthesis of 3,4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones.

Authors:  Takanori Matsuda; Masanori Shigeno; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

5.  Sterically directed functionalization of aromatic C-H bonds: selective borylation ortho to cyano groups in arenes and heterocycles.

Authors:  Ghayoor A Chotana; Michael A Rak; Milton R Smith
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

6.  Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors:  Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

7.  Regioselective aromatic borylation in an inert solvent.

Authors:  M K Tse; J Y Cho; M R Smith
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

8.  Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of beta-carbolin-1-one mimic of pancratistatin.

Authors:  Tomas Hudlicky; Uwe Rinner; Kevin J Finn; Ion Ghiviriga
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

9.  Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent.

Authors:  Tatsuo Ishiyama; Yusuke Nobuta; John F Hartwig; Norio Miyaura
Journal:  Chem Commun (Camb)       Date:  2003-12-07       Impact factor: 6.222

10.  Total synthesis of norzoanthamine.

Authors:  Masaaki Miyashita; Minoru Sasaki; Izumi Hattori; Mio Sakai; Keiji Tanino
Journal:  Science       Date:  2004-06-17       Impact factor: 47.728
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