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Concise Approach to 1,4-Dioxygenated Xanthones via Novel Application of the Moore Rearrangement.

ABSTRACT: The rapid synthesis of 1,4-dioxygenated xanthones and related natural products employing the Moore rearrangement as a key transformation has been developed. The approach features an acetylide stitching step to unite a substituted squaric acid with a protected hydroxy benzaldehyde derivative to provide a key intermediate that undergoes facile Moore rearrangement to deliver a hydroxymethyl aryl quinone. Subsequent oxidation, hydroxy group deprotection and cyclization then affords highly functionalized xanthones. The utility of the approach was demonstrated by its application to a concise and efficient synthesis of the naturally-occurring xanthone 1. The structure of a natural product that had been named dulcisxanthone C was also corrected to that of the xanthone 1.

SUBMITTER: Nichols AL

PROVIDER: S-EPMC3432973 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Concise Approach to 1,4-Dioxygenated Xanthones via Novel Application of the Moore Rearrangement.

Nichols Alexander L AL Zhang Patricia P Martin Stephen F SF

Tetrahedron 20120901 37

The rapid synthesis of 1,4-dioxygenated xanthones and related natural products employing the Moore rearrangement as a key transformation has been developed. The approach features an acetylide stitching step to unite a substituted squaric acid with a protected hydroxy benzaldehyde derivative to provide a key intermediate that undergoes facile Moore rearrangement to deliver a hydroxymethyl aryl quinone. Subsequent oxidation, hydroxy group deprotection and cyclization then affords highly functional ...[more]

PMID: 22962501

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