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

Meng Yao Zhang; Russell A. Barrow

doi:10.1021/acs.orglett.7b00840

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

Meng Yao Zhang, Russell A. Barrow

Gulbali Research Institute

Australian National University

Research output: Contribution to journal › Letter › peer-review

22 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2302-2305
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.7b00840
Publication status	Published - 05 May 2017

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

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.",

author = "Zhang, {Meng Yao} and Barrow, {Russell A.}",

note = "Funding Information: This study was undertaken with the support of the ANU and an NHMRC project grant (1028092). M.Y.Z. acknowledges the ANU for an Australian Postgraduate Award. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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N1 - Funding Information: This study was undertaken with the support of the ANU and an NHMRC project grant (1028092). M.Y.Z. acknowledges the ANU for an Australian Postgraduate Award. Publisher Copyright: © 2017 American Chemical Society.

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N2 - 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.

AB - 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.

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

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