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Carpanone

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Carpanone

Carpanone
Identifiers
CAS number 26430-30-8
PubChem 291296
ChemSpider 21864720 YesY
Jmol-3D images Image 1
Properties
Molecular formula C20H18O6
Molar mass 354.35 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Carpanone is a naturally occurring organic compound first isolated from the Carpano tree (Cinnamomum sp.), from which it derives its name. It is classified as a lignan.[1]

Total synthesis

The first total synthesis of carpanone was published by O. L. Chapman et al. in 1971. The biomimetic synthesis comprises only two steps beginning with 2-allylsesamol; the key step is an intramolecular Diels-Alder reaction of two identical molecules, which are coupled using a palladium(II) chloride catalyst:


This reaction creates two new rings and forms five contiguous chiral centers.[2]

References

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