Literature DB >> 14518993

The intramolecular carboxyarylation approach to podophyllotoxin.

Aaron J Reynolds1, Andrew J Scott, Craig I Turner, Michael S Sherburn.   

Abstract

Since 1960, only seven plant-derived anticancer drugs have received FDA approval for commercial production. Two are semisynthetic derivatives of podophyllotoxin. This paper describes concise, highly convergent, and conceptually novel approaches to (-)-podophyllotoxin and its enantiomer. These highly convergent syntheses feature a late-stage domino radical reaction to install the lactone ring and the pendant trimethoxyphenyl group.

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Year:  2003        PMID: 14518993     DOI: 10.1021/ja0376588

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  Next generation sequencing in predicting gene function in podophyllotoxin biosynthesis.

Authors:  Joaquim V Marques; Kye-Won Kim; Choonseok Lee; Michael A Costa; Gregory D May; John A Crow; Laurence B Davin; Norman G Lewis
Journal:  J Biol Chem       Date:  2012-11-16       Impact factor: 5.157

2.  Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis.

Authors:  Youran Luo; Álvaro Gutiérrez-Bonet; Jennifer K Matsui; Madeline E Rotella; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  ACS Catal       Date:  2019-08-28       Impact factor: 13.084

3.  Synthesis of Novel Functionalized 4-Aza-2,3-Didehydropodophyllotoxin Derivatives with Potential Antitumor Activity.

Authors:  Ajay Kumar; Antonio E Alegria
Journal:  J Heterocycl Chem       Date:  2010-11       Impact factor: 2.193

4.  Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

Authors:  Nicholas A Weires; Yuriy Slutskyy; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-13       Impact factor: 15.336

Review 5.  Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

Authors:  Rebekah G Reynolds; Huong Quynh Anh Nguyen; Jordan C T Reddel; Regan J Thomson
Journal:  Nat Prod Rep       Date:  2022-03-23       Impact factor: 13.423

6.  Biological Activity of N-Hydroxyethyl-4-aza-2,3-didehydropodophyllotoxin Derivatives upon Colorectal Adenocarcinoma Cells.

Authors:  Christian Vélez; Beatriz Zayas; Ajay Kumar
Journal:  Open J Med Chem       Date:  2014-03

Review 7.  Recent applications of the (TMS)3SiH radical-based reagent.

Authors:  Chryssostomos Chatgilialoglu; Jacques Lalevée
Journal:  Molecules       Date:  2012-01-06       Impact factor: 4.411

8.  Insight into 2α-Chloro-2'(2',6')-(Di)Halogenopicropodophyllotoxins Reacting with Carboxylic Acids Mediated by BF3·Et2O.

Authors:  Lingling Fan; Xiaoyan Zhi; Zhiping Che; Hui Xu
Journal:  Sci Rep       Date:  2015-11-17       Impact factor: 4.379

  8 in total

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