4.7 Article

Total Synthesis of Isohericenone J via a Stille Coupling Reaction

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 83, Issue 5, Pages 1701-1705

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.9b01251

Keywords

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Funding

  1. Key R&D Project of Shandong Province [2018GSF118022]
  2. National Natural Science Foundation of China [21572154, 21772181, 81803344]
  3. NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]
  4. Fundamental Research Funds for the Central Universities [201612013]
  5. Qingdao Scientific and Technological Innovation Center for Marine Biomedicine Development Grant [2017-CXZX01-1-1]

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The first total synthesis of isohericenone J is reported. Key features of this synthetic strategy are a Friedel-Crafts reaction to construct the isobenzofuranone unit and a Pd-catalyzed Stille coupling reaction for the formation of the C5-C1' bond, generating the natural product, as well as one of its isomers, in 6.0% overall yield in eight steps. This strategy provides a foundation for the synthesis of challenging isobenzofuranone and isoindolinone-type derivatives.

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