Carpanone

From Wikipedia, the free encyclopedia
Carpanone
Other names

Cupanone

Identifiers
CAS number 26430-30-8 YesY
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 (77 °F), 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

  1. ↑ J. Mohandas, M. Slaytor, T.R. Watson (1969). "Trans-2-methoxy-4,5-methylenedioxypropenylbenzene (carpacin) from a Cinnamomum sp. from Bougainville". Aust. J. Chem. 22 (8): 1803–1804. doi:10.1071/CH9691803. 
  2. ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 95–97. ISBN 3-527-29284-5. 
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.