Literature DB >> 20687594

Pd-catalyzed assembly of spirooxindole natural products: a short synthesis of horsfiline.

Nina Deppermann1, Heike Thomanek, Alexander H G P Prenzel, Wolfgang Maison.   

Abstract

The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.

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Year:  2010        PMID： 20687594     DOI： 10.1021/jo101401z

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


  12 in total

1.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

Authors:  Maxim Ratushnyy; Nikita Kvasovs; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-06       Impact factor: 15.336

Review 3.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

4.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

5.  Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone.

Authors:  Chuqin Peng; Jiwei Ren; Jun-An Xiao; Honggang Zhang; Hua Yang; Yiming Luo
Journal:  Beilstein J Org Chem       Date:  2014-02-07       Impact factor: 2.883

6.  Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

Authors:  Nivesh Kumar; Santanu Ghosh; Subhajit Bhunia; Alakesh Bisai
Journal:  Beilstein J Org Chem       Date:  2016-06-08       Impact factor: 2.883

7.  Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer-Schuster Rearrangement, Anti-Michael Addition/C(sp3)-H Functionalization, and Azacyclization.

Authors:  Srinivasarao Yaragorla; Ravikrishna Dada; P Rajesh; Manju Sharma
Journal:  ACS Omega       Date:  2018-03-09

8.  Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines.

Authors:  Natarajan Arumugam; Abdulrahman I Almansour; Raju Suresh Kumar; Periyasami Govindasami; Dhaifallah M Al-Thamili; Rajapandian Krishnamoorthy; Vaiyapuri Subbarayan Periasamy; Ali A Alshatwi; S M Mahalingam; Shankar Thangamani; J Carlos Menéndez
Journal:  Molecules       Date:  2018-05-05       Impact factor: 4.411

Review 9.  Transition metal-catalyzed synthesis of spirooxindoles.

Authors:  P V Saranya; Mohan Neetha; Thaipparambil Aneeja; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

10.  Green oxidation of indoles using halide catalysis.

Authors:  Jun Xu; Lixin Liang; Haohao Zheng; Yonggui Robin Chi; Rongbiao Tong
Journal:  Nat Commun       Date:  2019-10-18       Impact factor: 14.919
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