Synthesis of Tetracyclic Core Structure of Daphnezomines A and B

doi:10.6023/cjoc202208014

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 171-177.DOI: 10.6023/cjoc202208014 Previous Articles Next Articles

ARTICLES

Daphnezomines A和B的四环核心骨架合成

胡晶平^a^,^b, 陈文清^b, 蒋宇旸^b, 徐晶^b^,^c^,^*()

a 哈尔滨工业大学化工与化学学院哈尔滨 150001
b 南方科技大学化学系与格拉布斯研究院广东省催化化学重点实验室深圳市小分子药物发现与合成重点实验室广东深圳 518055
c 深圳湾实验室广东深圳 518132

收稿日期:2022-08-13 修回日期:2022-09-02 发布日期:2022-10-10
通讯作者: 徐晶
基金资助:
国家自然科学基金(21971104); 广东省教育厅高校重点科研项目(2021ZDZX2035); 深圳湾实验室(SZBL2019062801006); 深圳市诺贝尔奖科学家实验室(C17783101); 广东省本土创新团队项目(2019BT02Y335); 广东省高校创新团队(2020KCXTD016); 广东省催化化学重点实验室(2020B121201002); 深圳市科技创新委员会(ZDSYS20190902093215877)

Synthesis of Tetracyclic Core Structure of Daphnezomines A and B

Jingping Hu^a^,^b, Wenqing Chen^b, Yuyang Jiang^b, Jing Xu^b^,^c()

a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
b Department of Chemistry and Shenzhen Grubbs Institute Guangdong Provincial Key Laboratory of Catalysis Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Southern University of Science and Technology, Shenzhen, Guangdong 518055
c Shenzhen Bay Laboratory, Shenzhen, Guangdong 518132

Received:2022-08-13 Revised:2022-09-02 Published:2022-10-10
Contact: Jing Xu
Supported by:
National Natural Science Foundation of China(21971104); Key Research Projects in Colleges and Universities of Education Department of Guangdong Province(2021ZDZX2035); Shenzhen Bay Laboratory(SZBL2019062801006); Shenzhen Nobel Prize Scientists Laboratory Project(C17783101); Guangdong Innovative Program(2019BT02Y335); Innovative Team of Universities in Guangdong Province(2020KCXTD016); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Shenzhen Science and Technology Innovation Committee(ZDSYS20190902093215877)

1. .pdf(2010KB)

Abstract

Among the tiniest Daphniphyllum alkaloid subfamilies, daphnezomine A-type alkaloids consist of only three known members, namely daphnezomine A (1), daphnezomine B (2) and dapholdhamine B. These alkaloids contain a unique aza-adamantane core along with nine contiguous stereogenic centers, thus presenting remarkable synthetic challenges. The synthesis of tetracyclic core structure of 1 and 2 was reported. The key steps in our approach include a Huang’s amide-activa tion-annulation and a Hutchins-Kabalka reductive rearrangement.

Key words: total synthesis, Daphniphyllum alkaloids, daphnezomine A, daphnezomine B, aza-adamantane, Huang' s amide-activation-annulation, Hutchins-Kabalka reductive rearrangement

Cite this article

Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 25

[1]	(a) Li, Z.-Y.; Guo, Y.-W. Chin. J. Org. Chem. 2007, 27, 565. (in Chinese) doi: 10.1002/cjoc.200990092
	(李震宇, 郭跃伟, 有机化学, 2007, 27, 565.)
	(b) Liang, X.; Yang, X.-Z.; Chen, L.; Jiang, S.; Chen, Y.-D.; Deng, Q.-Y.; Chen, X.-G.; Yuan, J.-Q. Med. Chem. Res. 2020, 30, 1. doi: 10.1007/s00044-020-02646-w
	(c) Wu, H.; Zhang, X.; Ding, L.; Chen, S.; Yang, J.; Xu, X. Planta Med. 2013, 79, 1589. doi: 10.1055/s-0033-1351024
	(d) Xu, J. B.; Zhang, H.; Gan, L. S.; Han, Y. S.; Wainberg, M. A.; Yue, J. M. J. Am. Chem. Soc. 2014, 136, 7631. doi: 10.1021/ja503995b
[2]	(a) Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936. doi: 10.1039/b813006j pmid: 28205435
	(b) Chattopadhyay, A. K.; Hanessian, S. Chem. Rev. 2017, 117, 4104. doi: 10.1021/acs.chemrev.6b00412 pmid: 28205435
	(c) Kang, B.; Jakubec, P.; Dixon, D. J. Nat. Prod. Rep. 2014, 31, 550. doi: 10.1039/C3NP70115H pmid: 28205435
	(d) Guo, L.-D.; Chen, Y.; Xu, J. Acc. Chem. Res. 2020, 53, 2726. doi: 10.1021/acs.accounts.0c00532 pmid: 28205435
	(e) Zhong, J.; Wang, H.; Zhang, Q.; Gao, S. Alkaloids: Chem. Biol. 2021, 85, 113. pmid: 28205435
[3]	(a) Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532. pmid: 17818314
	(b) Heathcock, C. H.; Davidsen, S. K.; Mills, S.; Sanner, M. A. J. Am. Chem. Soc. 1986, 108, 5650. doi: 10.1021/ja00278a061 pmid: 17818314
	(c) Ruggeri, R. B.; Heathcock, C. H. J. Org. Chem. 1990, 55, 3714. doi: 10.1021/jo00299a006 pmid: 17818314
	(d) Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120. doi: 10.1021/jo00110a013 pmid: 17818314
	(e) Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734. doi: 10.1021/ja00234a046 pmid: 17818314
	(f) Stafford, J. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5433. doi: 10.1021/jo00307a006 pmid: 17818314
	(g) Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575. doi: 10.1021/jo00035a011 pmid: 17818314
	(h) Ruggeri, R. B.; McClure, K. F.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 1530. doi: 10.1021/ja00186a075 pmid: 17818314
[4]	Weiss, M. E.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 11501. doi: 10.1002/anie.201104681
[5]	(a) Lu, Z. Y.; Li, Y.; Deng, J.; Li, A. Nat. Chem. 2013, 5, 679. doi: 10.1038/nchem.1694
	(b) Li, J.; Zhang, W. H.; Zhang, F.; Chen, Y.; Li, A. J. Am. Chem. Soc. 2017, 139, 14893. doi: 10.1021/jacs.7b09186
	(c) Chen, Y.; Zhang, W. H.; Ren, L.; Li, J.; Li, A. Angew. Chem., Int. Ed. 2018, 57, 952. doi: 10.1002/anie.201711482
	(d) Zhang, W. H.; Ding, M.; Li, J.; Guo, Z. C.; Lu, M.; Chen, Y.; Liu, L. C.; Shen, Y. H.; Li, A. J. Am. Chem. Soc. 2018, 140, 4227. doi: 10.1021/jacs.8b01681
[6]	(a) Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2014, 136, 870. doi: 10.1021/ja411539w pmid: 25756504
	(b) Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2015, 137, 3510. doi: 10.1021/ja503899t pmid: 25756504
[7]	Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T. Angew. Chem.,Int. Ed. 2016, 55, 6067. doi: 10.1002/anie.201601958
[8]	Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen, Q. N. N.; Paton, R. S.; Dixon, D. J. J. Am. Chem. Soc. 2017, 139, 17755. doi: 10.1021/jacs.7b10956
[9]	Chen, X.; Zhang, H.-J.; Yang, X.; Lv, H.; Shao, X.; Tao, C.; Wang, H.; Cheng, B.; Li, Y.; Guo, J.; Zhang, J.; Zhai, H. Angew. Chem.,Int. Ed. 2018, 57, 947. doi: 10.1002/anie.201709762
[10]	(a) Xu, B.; Wang, B.; Xun, W.; Qiu, F. G. Angew. Chem.,Int. Ed. 2019, 58, 5754. doi: 10.1002/anie.201902268
	(b) Wang, B.; Xu, B.; Xun, W.; Guo, Y.; Zhang, J.; Qiu, F. G. Angew. Chem., Int. Ed. 2021, 60, 9439. doi: 10.1002/anie.202016212
[11]	Zhong, J.; Chen, K.; Qiu, Y.; He, H.; Gao, S. Org. Lett. 2019, 21, 3741. doi: 10.1021/acs.orglett.9b01184
[12]	(a) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Am. Chem. Soc. 2019, 141, 8431. doi: 10.1021/jacs.9b03576 pmid: 31533427
	(b) Hugelshofer, C. L.; Palani, V.; Sarpong, R. J. Org. Chem. 2019, 84, 14069. doi: 10.1021/acs.joc.9b02223 pmid: 31533427
[13]	Xu, G.; Wu, J.; Li, L.; Lu, Y.; Li, C. J. Am. Chem. Soc. 2020, 142, 15240. doi: 10.1021/jacs.0c06717
[14]	Cao, M.-Y.; Ma, B.-J.; Gu, Q.-X.; Fu, B.; Lu, H.-H. J. Am. Chem. Soc. 2022, 144, 5750. doi: 10.1021/jacs.2c01674
[15]	Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem.,Int. Ed. 2016, 55, 2577. doi: 10.1002/anie.201510861
[16]	(a) Chen, Y.; Hu, J.; Guo, L.-D.; Zhong, W.; Ning, C.; Xu, J. Angew. Chem., Int. Ed. 2019, 58, 7390. doi: 10.1002/anie.201902908
	(b) Guo, L.-D.; Hou, J.; Tu, W.; Zhang, Y.; Zhang, Y.; Chen, L.; Xu, J. J. Am. Chem. Soc. 2019, 141, 11713. doi: 10.1021/jacs.9b05641
	(c) Guo, L.-D.; Hu, J.; Zhang, Y.; Tu, W.; Zhang, Y.; Pu, F.; Xu, J. J. Am. Chem. Soc. 2019, 141, 13043. doi: 10.1021/jacs.9b07558
	(d) Guo, L.-D.; Zhang, Y.; Hu, J.; Ning, C.; Fu, H.; Chen, Y.; Xu, J. Nat. Commun. 2020, 11, 3538. doi: 10.1038/s41467-020-17350-x
	For our very recent total syntheses of other Daphniphyllum alkaloids, see:
	(e) Zhang, Y.; Chen, Y.; Song, M.; Tan, B.; Jiang, Y.; Yan, C.; Jiang, Y.; Hu, X.; Zhang, C.; Chen, W.; Xu, J. J. Am. Chem. Soc. 2022, 144, 16042. doi: 10.1021/jacs.2c05957
	(f) Hu, J.; Guo, L.-D.; Chen, W.; Jiang, Y.; Pu, F.; Ning, C.; Xu, J. Org. Lett. 2022, 24, 7416. doi: 10.1021/acs.orglett.2c02988
[17]	Morita, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 1999, 64, 7208. doi: 10.1021/jo990882o
[18]	Zhang, Y.; Di, Y.-T.; Mu, S.-Z.; Li, C.-S.; Zhang, Q.; Tan, C.-J.; Zhang, Z.; Fang, X.; Hao, X.-J. J. Nat. Prod. 2009, 72, 1325. doi: 10.1021/np900112d pmid: 19441852
[19]	(a) Wu, D.-P.; He, Q.; Chen, D.-H.; Ye, J.-L.; Huang, P.-Q. Chin. J. Chem. 2019, 37, 315. doi: 10.1002/cjoc.201900035
	(b) Huang, P.-Q.; Huang, Y.-H. Chin. J. Chem. 2017, 35, 613. doi: 10.1002/cjoc.201600700
	(c) Huang, P. -, Q.; Huang, Y.-H.; Wang, S.-R. Org. Chem. Front. 2017, 4, 431. doi: 10.1039/C6QO00720A
	(d) Huang, P.-Q.; Huang, Y.-H.; Geng, H.; Ye, J.-L. Sci. Rep. 2016, 6, 28801. doi: 10.1038/srep28801
[20]	(a) Hutchins, R. O.; Kacher, M.; Rua, L. J. Org. Chem. 1975, 40, 923. doi: 10.1021/jo00895a024
	(b) Kabalka, G. W.; Yang, D. T. C.; Baker, J. D. J. Org. Chem. 1976, 41, 574. doi: 10.1021/jo00865a043
[21]	Crystallographic data for compound C₉-epi-4 (CCDC 2170411) has been deposited at the Cambridge Crystallographic Data Centre.
[22]	Yang, J.; Xiong, Z.; Chen, Y.; Li, Y. Synth. Commun. 1997, 27, 2985. doi: 10.1080/00397919708005005
[23]	Wang, Z. Meinwald Rearrangement. In Comprehensive Organic Name Reactions and Reagents, Wiley Online Library, Hoboken, NJ, USA, 2010, pp. 1880-1882.
[24]	Crystallographic data for compound 14 (CCDC 2170422) has been deposited at the Cambridge Crystallographic Data Centre.
[25]	For our recent synthesis and studies of other caged natural products, see: pmid: 29364591
	(a) Xie, S. Ning, C.; Yu, Q.; Hou, J.; Xu, J. Chin. J. Chem. 2021, 39, 137. doi: 10.1002/cjoc.202000460 pmid: 29364591
	(b) Xie, S.; Chen, G.; Yan, H.; Hou, J.; He, Y.; Zhao, T.; Xu, J. J. Am. Chem. Soc. 2019, 141, 3435. doi: 10.1021/jacs.9b00391 pmid: 29364591
	(c) Zhang, Y.; Guo, L.-D.; Xu, J. Chin. J. Org. Chem. 2019, 39, 1079. (in Chinese) pmid: 29364591
	(张焱, 郭联东, 徐晶, 有机化学, 2019, 39, 079.) pmid: 29364591
	(d) Zhao, N.; Yin, S.; Xie, S.; Yan, H.; Ren, P.; Chen, G.; Chen, F.; Xu, J. Angew. Chem. Int. Ed. 2018, 57, 3386. doi: 10.1002/anie.201800167 pmid: 29364591

Daphnezomines A和B的四环核心骨架合成

Synthesis of Tetracyclic Core Structure of Daphnezomines A and B

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 25

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[2]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[3]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[4]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[5]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[6]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[7]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[8]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[9]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[10]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[11]	Lu Guo, Pingping Tang. Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3816-3825.
[12]	Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577.
[13]	Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730.
[14]	Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562.
[15]	Sun Zezhong, Xu Miao, Wang Yunxia, Hu Xiangdong. Synthetic Progress of Alkaloids against Mycobacterium Tuberculosis: Pseudopteroxazole and Ileabethoxazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4203-4215.