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(S)-Ipsdienol

(S)-Ipsdienol is a terpene alcohol. It is one of the major aggregation pheromones of the bark beetle. It was first identified from Ips confusus, in which it is believed to be a principle sex attractant. It is suggested that the compound plays a role in interspecies communication between Ips latidens and Ips ini, facilitating reductions in competition for breeding material and/or mating interference.

Synthesis

The compound has been synthesized from D-mannitol. Alternative syntheses were realized through the asymmetric isoprenylation of correspondent aldehyde (prenal) and alcohol (prenol). Chiral resolution of racemic precursor has been found to provide both enantiomers of ipsdienol in high enantiomeric purity and in preparative scale.

References

References

  1. (October 1966). "Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine". Science.
  2. (1 August 1991). "Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae)". Journal of Chemical Ecology.
  3. Hanessian, Stephen. (1983). "Total Synthesis of Natural Products: The 'Chiron' Approach". Pergamon press.
  4. (2019). "Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid". Advanced Synthesis & Catalysis.
  5. (2019). "Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer". Chemical Communications.
  6. (2016). "Improved synthesis of optically active ipsdienol". Russian Journal of Organic Chemistry.
  7. (2012). "Stereoselective synthesis of (''R'')- and (''S'')-Ipsdienols, pheromone components of bark beetles of the ''Ips'' family". Russian Journal of Organic Chemistry.
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monoterpenes insect-pheromones secondary-alcohols enols
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