Ring Expansions Within the Gold-Catalyzed Cycloisomerization of O-Tethered 1,6-Enynes. Application to the Synthesis of Natural-Product-like Macrocycles

Authors

  • Dr. Antoine Simonneau,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Dr. Youssef Harrak,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Louis Jeanne-Julien,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Dr. Gilles Lemière,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Dr. Virginie Mouriès-Mansuy,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Dr. Jean-Philippe Goddard,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Prof. Dr. Max Malacria,

    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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  • Prof. Dr. Louis Fensterbank

    Corresponding author
    1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
    • Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), UPMC Univ Paris 06, Sorbonne Université, 4 place Jussieu, C. 229, 75005 Paris (France), Fax: (+33) 144273078
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Abstract

original image

Goldenyne: O-tethered 1,6-enynes that contain a strained ring at the 3 position can cycloisomerize upon cationic gold(I) catalysis through a ring-expansion process. A two-step sequence allows the transformation of the cyclized compounds into ketomacrolactones, which are reminiscent of natural products.

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