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Enantioselective Synthesis of Azamerone

preprint
revised on 28.11.2018 and posted on 28.11.2018 by Matthew L. Landry, Grace McKenna, Noah Burns
A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of 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.

Funding

NIH R01 GM114061

NSF GRF to M.L.L.

History

Email Address of Submitting Author

nburns@stanford.edu

Institution

Stanford University

Country

USA

ORCID For Submitting Author

0000-0003-1064-4507

Declaration of Conflict of Interest

The authors declare no conflicts of interest

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in Journal of the American Chemical Society

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