Total synthesis of (+)-arteanniun M using the tandem oxy-Cope/ene reaction

L Barriault; D H Deon

doi:10.1021/ol015970l

Total synthesis of (+)-arteanniun M using the tandem oxy-Cope/ene reaction

Org Lett. 2001 Jun 14;3(12):1925-7. doi: 10.1021/ol015970l.

Authors

L Barriault¹, D H Deon

Affiliation

¹ Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada, K1N 6N5. lbarriau@science.uottawa.ca

PMID: 11405746
DOI: 10.1021/ol015970l

Abstract

[see reaction]. The first total synthesis of (+)-arteannuin M was accomplished using the tandem oxy-Cope/transannular ene reaction as the key step to construct the bicyclic core of the natural product. The tandem reaction proceeded with high diastereo- and enantiomeric excess.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Artemisinins*
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Stereoisomerism

Substances

Artemisinins
Sesquiterpenes
artemisinin