Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae

J Org Chem. 2021 Apr 2;86(7):5245-5254. doi: 10.1021/acs.joc.1c00145. Epub 2021 Mar 16.

Abstract

The uncommon jasmone derivatives dehydrojasmone, isojasmol, and isojasmyl acetate, floral scent compounds from night-blooming Araceae, were synthesized in a scalable synthesis employing conjugate addition with a selenoacetal as the key step. The stereoselective strategy with subsequent enzymatic kinetic resolution allowed determining the absolute configuration of the natural compounds by GC on a chiral phase. The homoterpene (E)-4,8-dimethyl-1,3,7-nonatrien-5-yl acetate, another uncommon scent compound, was obtained by α-regioselective aldehyde prenylation. The biological activities of dehydrojasmone and isojasmol were investigated in field assays, showing that these unique volatiles are able to selectively attract specific cyclocephaline scarab beetle pollinators.

MeSH terms

  • Araceae*
  • Flowers
  • Odorants
  • Pheromones
  • Pollination
  • Volatile Organic Compounds*

Substances

  • Pheromones
  • Volatile Organic Compounds