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Accessing Polyoxygenated Dibenzofurans via the Union of Phenols and o-Benzoquinones: Rapid Syntheses of Metabolites Isolated from Ribes takare

Author:
Zhang, Meng Yao, Barrow, Russell A.
Source:
Organic letters 2017 v.19 no.9 pp. 2302-2305
ISSN:
1523-7052
Subject:
Ribes, benzoquinones, carbon, chemical reactions, chemical structure, dibenzofuran, metabolites, naphthols
Abstract:
The construction of polyoxygenated dibenzo[b,d]furan frameworks from the union of substituted phenols/naphthols and o-benzoquinones via a Michael-oxidation-oxa-Michael cascade is reported. The power of this transformation is demonstrated in the generation of a library of highly substituted dibenzofurans, featuring specifically substituted molecules containing broad ranges of functionality. The utility of this method is showcased in the total syntheses of two dibenzofurans isolated from Ribes takare, assembling the carbon scaffold of both natural products in one operation.
Agid:
5794042