Application of Pd-Catalyzed C-H Alkylation Reaction in Total Syntheses of Twelve Amicoumacin-Type Natural Products

  • Org Lett. 2021 Sep 3;23(17):6956-6960. doi: 10.1021/acs.orglett.1c02576.
Hui-Hong Wang  1 ,  Zhao Li  2 ,  Yi-Yue Feng  2 ,  Gao-Feng Yin  2 ,  Tao Shi  2 ,  Dian He  2 ,  Xiao-Dong Wang  2 ,  Zhen Wang  2  1
Affiliations
  • 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, No. 222 South Tianshui Road, Lanzhou 730000, China.
  • 2. School of Pharmacy, Lanzhou University, No. 199 West Donggang Road, Lanzhou 730000, China.
PMID: 34424725 DOI: 10.1021/acs.orglett.1c02576
Abstract

Enantioselective total syntheses of 12 amicoumacin-type natural products are accomplished with a palladium(II)-catalyzed C-H alkylation as the key step to furnish the 3,4-dihydroisocoumarin scaffold. The target chemicals are assembled in a convergent protocol by merging 3,4-dihydroisocoumarin derived amine part with categories of acid segments that are efficiently prepared by chemoselective catalytic oxidation of chiral 1,2-dihydroxyethylfuran-2(5H)-ones. Afterward, the cytotoxicity of amicoumacins on five Cancer cell lines and one normal cell line is investigated.

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