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Keywords:

  • biosyntheses;
  • Cope rearrangements;
  • pericyclic reactions;
  • pheromones
Thumbnail image of graphical abstract

A pheromone roughly 100 times more effective than cyclohepta-1,4-diene 2 (R = C2H5, ectocarpene) is its biosynthetic precursor 1. This thermally labile cis-disubstituted cyclopropane is the actual signaling agent of the marine brown algae Ectocarpus siliculosus. The [3,3]sigmatropic rearrangement of 1 giving 2 (t1/2 = 21 min at 18°C) is the fastest known reaction for the spontaneous inactivation of a pheromone.