Total Synthesis and Structure Revision of Palmarumycin B6

J Nat Prod. 2018 Aug 24;81(8):1803-1809. doi: 10.1021/acs.jnatprod.8b00258. Epub 2018 Aug 13.

Abstract

Palmarumycin B6 and its regioisomer were synthesized via 7- and 13-step routes using 2-chlorophenol and 4-chlorophenyl methyl ether as the starting materials in overall yields of 2.7% and 12%, respectively. Their structures were characterized by 1H and 13C NMR, HRESIMS, and X-ray diffraction data. The structure of palmarumycin B6 was revised as 6-chloropalmarumycin CP17. The bioassay results showed that the larvicidal activity of palmarumycin B6 with an LC50 value of 32.7 μM was significantly higher than that of its 8-chloro isomer, with an LC50 value of 227.3 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Insecticides / chemical synthesis
  • Insecticides / chemistry*
  • Insecticides / toxicity
  • Larva / drug effects
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry*
  • Naphthalenes / toxicity
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Spiro Compounds / toxicity
  • Structure-Activity Relationship
  • X-Ray Diffraction

Substances

  • Insecticides
  • Naphthalenes
  • Plant Extracts
  • Spiro Compounds
  • palmarumycin b6