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Carpanone

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Carpanone
Names
Other names Cupanone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H18O6/c1-9-3-11-13(21)5-17-20(25-8-24-17)19(11)18(10(9)2)12-4-15-16(23-7-22-15)6-14(12)26-20/h3-6,9-10,18-19H,7-8H2,1-2H3/t9-,10+,18+,19+,20?/m0/s1Key: WTXORUUTAZJKSN-JMAAQRFFSA-N
  • InChI=1/C20H18O6/c1-9-3-11-13(21)5-17-20(25-8-24-17)19(11)18(10(9)2)12-4-15-16(23-7-22-15)6-14(12)26-20/h3-6,9-10,18-19H,7-8H2,1-2H3/t9-,10+,18+,19+,20?/m0/s1Key: WTXORUUTAZJKSN-JMAAQRFFBX
SMILES
  • CC1C=C2C3C(C1C)c4cc5c(cc4OC36C(=CC2=O)OCO6)OCO5
Properties
Chemical formula C20H18O6
Molar mass 354.343 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

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: 1803–1804. doi:10.1071/CH9691803.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Nicolaou, K. C. (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 95–97. ISBN 3-527-29284-5. {{cite book}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
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