Chinese Journal of Organic Chemistry >
Studies toward the Total Synthesis of Xanthochymol
Received date: 2021-06-03
Revised date: 2021-07-08
Online published: 2021-08-10
Supported by
National Natural Science Foundation of China(81973438)
Xanthochymol, a polycyclic polyprenylated acylphloroglucinol (PPAP) natural compound, has demonstrated good anticancer and antimicrobial properties. However, no related studies on the synthesis of xanthochymol have been reported hitherto. In this study, 3,3-dimethylglutaric acid was used as the starting material to synthesize a key linear precursor via several steps, followed by a domino Dieckmann condensation reaction to construct the bicyclo[3.3.1]nonane-2,4,9-trione core skeleton. With that, the total synthesis of (±)-xanthochymol in 11 steps with a total yield of 10% has been first accomplished. By obtaining the side chain diastereomers of xanthochymol through this study, we have clarified the difference between them on the 1H NMR and 13C NMR spectra while at the same time provided references for future isolation, identification, and discrimination of xanthochymol from its side chain structural isomers.
Xueying Wang , Yee Lin Phang , Changwu Zheng , Hongxi Xu . Studies toward the Total Synthesis of Xanthochymol[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4421 -4427 . DOI: 10.6023/cjoc202106009
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