World Library  
Flag as Inappropriate
Email this Article


Article Id: WHEBN0022792515
Reproduction Date:

Title: Carpanone  
Author: World Heritage Encyclopedia
Language: English
Publisher: World Heritage Encyclopedia


CAS number 26430-30-8
PubChem 291296
ChemSpider 21864720 YesY
Jmol-3D images Image 1
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]


This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Hawaii eBook Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.