Reductive aromatization of quinols: synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin.
[reaction: see text] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment with mCPBA afforded the tricyclic papulacandin framework. Alternatively, hydroboration gave the chaetiacandin nucleus.
Parker
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Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA. kathlyn_parker@brown.edu
Georges
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D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D054714:Echinocandins; D006027:Glycosides / Q000138:chemical synthesis*; D006873:Hydroquinones / Q000737:chemistry*; D008969:Molecular Sequence Data
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D054714:Echinocandins; D006027:Glycosides; D006873:Hydroquinones; C014732:papulacandins; C045691:chaetiacandin