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Enantioselective Synthesis of Azamerone.

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.

SUBMITTER: Landry ML

PROVIDER: S-EPMC6497086 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of Azamerone.

Landry Matthew L ML McKenna Grace M GM Burns Noah Z NZ

Journal of the American Chemical Society 20190208 7

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 ca ...[more]

PMID: 30707836

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