1321576-08-2Relevant academic research and scientific papers
Concise approach to 1,4-dioxygenated xanthones via novel application of the Moore rearrangement
Nichols, Alexander L.,Zhang, Patricia,Martin, Stephen F.
, p. 7591 - 7597 (2012/09/21)
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.
General and expedient synthesis of 1,4-dioxygenated xanthones
Nichols, Alexander L.,Zhang, Patricia,Martin, Stephen F.
, p. 4696 - 4699 (2011/10/09)
A facile entry to 1,4-dioxygenated xanthones having a variety of substitution patterns and substituents was developed that features a novel application of the Moore cyclization using substrates that were readily assembled in a highly convergent fashion by an acetylide stitching process. The practical utility of the methodology was demonstrated by an efficient synthesis of a naturally occurring xanthone and correction of the structure of dulcisxanthone C.
