Asymmetric Synthesis of All Stereoisomers of the Strigol Analogue GR24. Dependence of Absolute Configuration on Stimulatory Activity of Striga hermonthica and Orobanche crenata Seed Germination

Parasitic weeds belonging to the genera Striga, Orobanche, and Alectra cause severe damage to several graminaceous and leguminous crops in tropical and semitropical areas of the eastern hemisphere

Jan Willem J. F. Thuring; Gerard H. L. Nefkens; Binne Zwanenburg

2002

Scholarcy highlights

  • Parasitic weeds belonging to the genera Striga, Orobanche, and Alectra cause severe damage to several graminaceous and leguminous crops in tropical and semitropical areas of the eastern hemisphere
  • Seeds of these parasitic weeds usually remain dormant in the soil, but after exposure to a specific germination stimulant, which is exuded by the roots of a suitable host, the seeds germinate and attach to the root system of the host
  • The present paper deals with the asymmetric syntheses of all four stereoisomers of GR24 and their germination activities on seeds of Striga hermonthica Benth and Orobanche crenata Forsk
  • The route that requires the homochiral latent D-rings 6 and ent 6 is generally applicable in the enantioselective synthesis of strigol analogues
  • Seeds of O. crenata were exposed to an aqueous solution of sodium hypochlorite for 5 min with agitation
  • The relative importance of the absolute configuration at the different stereogenic centers in GR24 for the germination stimulatory activity has been assessed, indicating that the molecular shape is determined by the combination of all stereocenters

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