title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165.
authors.forename: Alexander L
authors.initials: AL
authors.lastname: Nichols
authors.forename: Patricia
authors.initials: P
authors.lastname: Zhang
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin