Literature DB >> 25313860

Total syntheses of menisporphine and daurioxoisoporphine C enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium salt.

Jing Zhang1, Jie Chen, Xiaoyun Zhang, Xiaoguang Lei.   

Abstract

Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.

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Year:  2014        PMID: 25313860     DOI: 10.1021/jo5020432

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

Authors:  Jian Jin; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-02       Impact factor: 15.336

2.  Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes.

Authors:  Jorge Castellanos-Soriano; Daniel Álvarez-Gutiérrez; M Consuelo Jiménez; Raúl Pérez-Ruiz
Journal:  Photochem Photobiol Sci       Date:  2022-03-18       Impact factor: 4.328

Review 3.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

4.  Photochemical C-H arylation of heteroarenes for DNA-encoded library synthesis.

Authors:  Matthias Krumb; Lisa Marie Kammer; Shorouk O Badir; María Jesús Cabrera-Afonso; Victoria E Wu; Minxue Huang; Adam Csakai; Lisa A Marcaurelle; Gary A Molander
Journal:  Chem Sci       Date:  2021-12-21       Impact factor: 9.825

Review 5.  Traditional and sustainable approaches for the construction of C-C bonds by harnessing C-H arylation.

Authors:  Jagrit Grover; Gaurav Prakash; Nupur Goswami; Debabrata Maiti
Journal:  Nat Commun       Date:  2022-02-28       Impact factor: 14.919

6.  A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines.

Authors:  Benedikt C Melzer; Franz Bracher
Journal:  Beilstein J Org Chem       Date:  2017-08-08       Impact factor: 2.883

  6 in total

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