Enantioselective Synthesis of Azamerone

28 November 2018, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Total Synthesis
Enantioselective Halogenation
Natural Products

Supplementary materials

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Azamerone Supporting Information ChemRxiv
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su1811
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nzb stanford finished
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su1809
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su1713
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su1412
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su1411a
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