(''S'')-Ipsdienol is a

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

. It is one of the major aggregation pheromones of the

bark beetle A bark beetle is the common name for the subfamily of beetles Scolytinae. Previously, this was considered a distinct family (Scolytidae), but is now understood to be a specialized clade of the "true weevil" family (Curculionidae). Although th ...

. 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 Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenoids. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used occ ...

Chiral resolution Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term wit ...

of racemic precursor has been found to provide both

enantiomers In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

of ipsdienol in high enantiomeric purity and in preparative scale.

References

{{DEFAULTSORT:Ipsdienol, (S)- Monoterpenes Insect pheromones Secondary alcohols Enols