Work

Enantioselective Synthesis of Azamerone

Year: 2019

Type: article

Abstract: A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of natural-product-relevant chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.8b12566

Authors: Matthew L. Landry, Grace M. McKenna, Noah Z. Burns

Institution: Stanford University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Stanford University, National Institute of General Medical Sciences, Division of Graduate Education

Awards: Selective Halogenation Reactions for the Synthesis of Chiral Bioactive Small Molecules, G736622850