Studies toward the Total Synthesis of Xanthochymol

doi:10.6023/cjoc202106009

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4421-4427.DOI: 10.6023/cjoc202106009 Previous Articles Next Articles

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大叶藤黄醇的全合成研究

王学颖, 盘伊琳, 郑昌武^*(), 徐宏喜^*()

上海中医药大学中药学院上海 201203

收稿日期:2021-06-03 修回日期:2021-07-08 发布日期:2021-08-09
通讯作者: 郑昌武, 徐宏喜
基金资助:
国家自然科学基金(81973438)

Studies toward the Total Synthesis of Xanthochymol

Xueying Wang, Yee Lin Phang, Changwu Zheng(), Hongxi Xu()

School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203

Received:2021-06-03 Revised:2021-07-08 Published:2021-08-09
Contact: Changwu Zheng, Hongxi Xu
Supported by:
National Natural Science Foundation of China(81973438)

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Abstract

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.

Key words: polycyclic polyprenylated acylphloroglucinols (PPAPs), bicyclo[3.3.1]nonanes, Dieckmann condensation, domino reaction

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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.

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Fig. & Tab. 5

Figure 1. Xanthochymol and its isomers

Scheme 1. Retrosynthetic analysis of xanthochymol

Scheme 2. Competitive ring-opening reaction of compound 13

Scheme 3. Synthesis of bicyclo[3.3.1]nonane ring

Scheme 4. Synthesis of xanthochymol

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大叶藤黄醇的全合成研究

Studies toward the Total Synthesis of Xanthochymol

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