A Convergent Approach to (−)-Callystatin A Based on Local Symmetry

Authors

  • Dr. Mathieu Candy,

    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    Search for more papers by this author
  • Dr. Loïc Tomas,

    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    Search for more papers by this author
  • Dr. Sabrina Parat,

    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    Search for more papers by this author
  • Dr. Virginie Heran,

    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    Search for more papers by this author
  • Dr. Hugues Bienaymé,

    1. TARGEON, 65 rue Rambuteau, 75004 Paris (France)
    Search for more papers by this author
  • Prof. Dr. Jean-Marc Pons,

    Corresponding author
    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    • Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87===

    Search for more papers by this author
  • Dr. Cyril Bressy

    Corresponding author
    1. Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87
    • Aix-Marseille Université, CNRS, iSm2 UMR7313, 13397 Marseille Cedex 20 - Service 532 (France), Fax: (+33) 04-91-28-91-87===

    Search for more papers by this author

Abstract

original image

The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (−)-callystatin A was developed assembling three fragments through Julia–Kocienski olefination and Stille cross-coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme).

Ancillary