%0 Generic %A Landry, Matthew L. %A McKenna, Grace M. %A Burns, Noah Z. %D 2019 %T Enantioselective Synthesis of Azamerone %U https://acs.figshare.com/articles/dataset/Enantioselective_Synthesis_of_Azamerone/7692155 %R 10.1021/jacs.8b12566.s001 %2 https://acs.figshare.com/ndownloader/files/14303516 %K motif %K dichlorinated meroterpenoid azamerone %K boronic hemiester %K enantioenriched forms %K cycloaddition %K quinone diazide %K novel enantioselective chloroetherification reaction %K tetrazine %K natural-product-relevant chiral organochlorides %K strategy %K tactic %K accessing %K paucity %K route features %K Azamerone %K late-stage %K cascade %K Enantioselective Synthesis %K synthesis %K Pd-catalyzed cross-coupling %X 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. %I ACS Publications