Three Rings in One Step: A Quick Approach to IKD-8344

Authors

  • Dr. Yang Zou,

    1. State Key Laboratory of Bioorganic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    Search for more papers by this author
  • Prof. Dr. Yikang Wu

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    • State Key Laboratory of Bioorganic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    Search for more papers by this author

  • This work was supported by the National Basic Research Program of China (the 973 Program, 2010CB833200) and the National Natural Science Foundation of China (21172247, 21032002, 20921091, 20621062).

Abstract

original image

A highly efficient enantioselective total synthesis of the natural antibiotic IKD-8344 is achieved through a convergent route. This route features an otherwise impossible concurrent formation of the THF rings from a linear polyketide precursor through intramolecular O alkylations of mesylates in competition with normally rather facile β elimination and/or α racemization reactions (see scheme, Ms=methanesulfonyl).

Ancillary