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      Asymmetric Chemoenzymatic Synthesis of (–)-Podophyllotoxin and Related Aryltetralin Lignans

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          Abstract

          (–)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Here, we report a short chemoenzymatic total synthesis of (–)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C–C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram scale access to (–)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

          Graphical Abstract

          Biocatalytic C–C coupling: Podophyllotoxin, a potent microtubule depolymerizing agent, was synthesized in a concise manner through a strategic use of three oxidative processes. Highlights of the route include a gram-scale biocatalytic C–C coupling to construct the tetracyclic core of the natural product and a chemoselective late-stage installation of the secondary alcohol at C7.

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          Author and article information

          Journal
          0370543
          537
          Angew Chem Int Ed Engl
          Angew. Chem. Int. Ed. Engl.
          Angewandte Chemie (International ed. in English)
          1433-7851
          1521-3773
          2 July 2019
          17 July 2019
          19 August 2019
          19 August 2020
          : 58
          : 34
          : 11657-11660
          Affiliations
          Department of Chemistry, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL 33458
          Author notes
          [[+]]

          These authors contributed equally to this work

          Article
          PMC6688964 PMC6688964 6688964 nihpa1039165
          10.1002/anie.201904102
          6688964
          31241812
          30bd551f-7f2b-410a-b5e2-428c58ea0831
          History
          Categories
          Article

          non-heme dioxygenase,biocatalysis,podophyllotoxin,total synthesis,aryltetralin lignans

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