Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 7, Pages 2867-2871Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b12566
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Funding
- Stanford University
- National Institutes of Health [R01 GM114061]
- National Science Foundation [DGE-114747 GRF]
- Center for Molecular Analysis and Design at Stanford (GRF)
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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.
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