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^*

^*Corresponding author for this work

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

26 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 - 5 May 2017

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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.",

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AU - Barrow, Russell A.

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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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DO - 10.1021/acs.orglett.7b00840

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ER -

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

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