Literature DB >> 15727461

Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter.

Naidu S Chowdari1, Carlos F Barbas.   

Abstract

A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through l-proline-derived, tetrazole-catalyzed direct asymmetric alpha-amination of 3-(4-bromophenyl)-2-methylpropanal with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed. [structure: see text]

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Year:  2005        PMID: 15727461     DOI: 10.1021/ol047368b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound.

Authors:  Masanori Kawasaki; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

2.  Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media.

Authors:  Jae Ho Shim; Seok Hyun Cheun; Hyeon Soo Kim; Deok-Chan Ha
Journal:  Molecules       Date:  2022-04-25       Impact factor: 4.927

Review 3.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

4.  111In-DANBIRT In Vivo Molecular Imaging of Inflammatory Cells in Atherosclerosis.

Authors:  Roberto Mota; Matthew J Campen; Matthew E Cuellar; William S Garver; Jacob Hesterman; Mohammed Qutaish; Tamara Daniels; Monique Nysus; Carston R Wagner; Jeffrey P Norenberg
Journal:  Contrast Media Mol Imaging       Date:  2018-11-13       Impact factor: 3.161

Review 5.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

Review 6.  Synthesis of polysubstituted arenes through organocatalytic benzannulation.

Authors:  Qian Zhao; Cheng Peng; Gu Zhan; Bo Han
Journal:  RSC Adv       Date:  2020-11-10       Impact factor: 4.036

7.  Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P1 agonist.

Authors:  Qiong Xiao; Yifan Tang; Ping Xie; Dali Yin
Journal:  RSC Adv       Date:  2019-10-18       Impact factor: 4.036

Review 8.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823

  8 in total

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