Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization

Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco Jr

doi:10.1021/ja052049g

Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization

J Am Chem Soc. 2005 Jul 6;127(26):9342-3. doi: 10.1021/ja052049g.

Authors

Jianglong Zhu¹, Nicholas P Grigoriadis, Jonathan P Lee, John A Porco Jr

Affiliation

¹ Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.

PMID: 15984841
DOI: 10.1021/ja052049g

Abstract

An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.

MeSH terms

Benzopyrans / chemical synthesis*
Catalysis
Copper / chemistry*
Ligands
Molecular Structure
Oxidation-Reduction
Pigments, Biological / chemical synthesis*
Solvents / chemistry
Stereoisomerism
Temperature

Substances

Benzopyrans
Ligands
Pigments, Biological
Solvents
azaphilone
Copper