ja8b12566_si_001.cif (874.98 kB)
Enantioselective Synthesis of Azamerone
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posted on 2019-02-01, 00:00 authored by Matthew
L. Landry, Grace M. McKenna, Noah Z. BurnsA 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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motifdichlorinated meroterpenoid azameroneboronic hemiesterenantioenriched formscycloadditionquinone diazidenovel enantioselective chloroetherification reactiontetrazinenatural-product-relevant chiral organochloridesstrategytacticaccessingpaucityroute featuresAzameronelate-stagecascadeEnantioselective SynthesissynthesisPd-catalyzed cross-coupling
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