Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids

doi:10.6023/cjoc202408006

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

Communesin生物碱核心五环骨架的高效合成

杨之同^a, 宋恒谦^a, 雷盼^a, 闫嘉航^a,*, 谢卫青^a,b,*

^a西北农林科技大学化学与药学院陕西杨凌 712100;
^b陕西省植物源农药研究与开发重点实验室陕西杨凌 712100

收稿日期:2024-08-06 修回日期:2024-09-09
基金资助:
国家自然科学基金(No. 22301245 , 22371231 )资助项目.

Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids

Zhitong Yang^a, Hengqian Song^a, Pan Lei^a, Jiahang Yan^a,*, Weiqing Xie^a,b,*

^aCollege of Chemistry & Pharmacy, Northwest A& F University, Yangling, Shaanxi 712100;
^bKey Laboratory of Botanical Pesticide R& D in Shaanxi Province, Yangling, Institution, Shaanxi 712100;

Received:2024-08-06 Revised:2024-09-09
Contact: * E-mail: xiewq@nwafu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22301245 , 22371231 )

1. .pdf(1104KB)

Abstract

Communesin alkaloids are a family of complex dimeric cyclotryptamine alkaloids isolated from the marine fungi of the genus Penicillium. These indole alkaloids contain a unique caged heptacyclic skeleton along with five stereogenic centers at least, two of which are the contiguous quaternary carbon centers (CQCCs), thus presenting remarkable synthetic challenges. Herein, we develop an expedient construction the core pentacyclic ring system of communesins. The key steps include a catalytic asymmetric conjugated addition promoted by Ni(II)/chiral N,O-chiral dioxide for establishing the CQCCs and a deprotection/ring-opening reaction/cyclization cascade for setting up the pentacyclic skeleton.

Key words: communesin, contiguous quaternary carbon, asymmetric catalysis, conjugated addition, cascade cyclization

Cite this article

Zhitong Yang, Hengqian Song, Pan Lei, Jiahang Yan, Weiqing Xie. Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202408006.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Numata A., Takahashi C., Ito Y., Takada T., Kawai K., Usami Y., Matsumura E., Imachi M., Ito T. Hasegawa T. Tetrahedron Lett. 1993, 34, 2355.
[2] Dalsgaard P.W., Blunt J. W., Munro Murray H. G., Frisvad J. C., Carsten Christophersen C. J. Nat. Prod. 2005, 68, 258.
[3] Jadulco R., Edrada R.A., Ebel R., Berg A., Schaumann K., Wray V., Steube K., Proksch P. J. Nat. Prod. 2004, 67, 78.
[4] Hayashi H., Matsumoto H., Akiyama K. Biosci. Biotechnol. Biohem. 2004, 68, 753.
[5] Yang J., Wu H., Shen L., Qin Y.J. Am. Chem. Soc., 2007, 129, 13794.
[6] (a) Zuo Z. W., Xie W. Q., Ma D. W. J. Am. Chem. Soc. 2010, 132, 13226.
(b) Zuo Z. W., Ma D. W. Angew. Chem. Int. Ed. 2011, 50, 12008.
[7] (a) Liu P., Seo J. H., Weinreb S. M. Angew. Chem. Int. Ed. 2010, 49, 2000.
(b) Seo J. H., Liu P., Weinreb S.M. J. Org. Chem. 2010, 75, 2667.
[8] Belmar J., Funk R.L. J. Am. Chem. Soc. 2012, 134, 16941.
[9] (a) Lathrop S. P, Pompeo M., Chang W. T, and Movassaghi M. J. Am. Chem. Soc. 2016, 138, 7763.
(b) Pompeo M., Cheah J. H., Movassaghi M. J. Am. Chem. Soc. 2019, 141, 14411.
[10] Park J., Jean A., Chen David Y.K. Angew. Chem. Int. Ed. 2017, 56, 14237.
[11] Liang X, Zhang T.Y., Zeng X. Y., Zheng Y., Wei K., Yang Y. R. J. Am. Chem. Soc. 2017, 139, 3364.
[12] For review on chiral N,N’-dioxide ligand: (a) Liu X. H., Lin L. L., Feng X. M. Org. Chem. Front. 2014, 1, 298.
(b) Liu X. H., Zheng H. F., Xia Y., Lin L. L., Feng X. M. Acc. Chem. Res. 2017, 50, 2621. For construction of contiguous quaternary carbon centers: (c) Zhang H. L., Hong L., Kang H., Wang R., J. Am. Chem. Soc. 2013, 135, 14098.
(d) Zheng J. F., Lin L. L., Dai L., Tang Q., Liu X. H., Feng X. M., Angew. Chem. Int. Ed. 2017, 56, 13107. (e) Xu J., Zhong Z. W., Jiang M. Y., Zhou Y. Q., Liu X. H., Feng X. M. CCS Chem. 2020, 2, 1894.
(f) Xu J., Li R. Z., Xu N., Liu X. H., Wang F., Feng X. M. Org. Lett. 2021, 23, 1856.
[13] Xie W.Q., Jiang G. D., Liu H., Hu J. D., Pan X. X., Zhang H., Wan X. L., Lai Y. S., Ma D. W. Angew. Chem. Int. Ed. 2013, 52, 12924.
[14] (a) Wei H. B., Chen G. Z., Zou H. H., Zhou Z. Q., Lei P., Yan J. H., Xie W. Q. Org. Chem. Front. 2021, 8, 3255.
(b) Huo J. Y., Li X. H., Chen Q. H., Gao P. P., Hou Y., Lei P., Zou H. H., Yan J. H., Wan X. L., Xie W. Q. ACS Catalysis. 2023, 13, 15007.
[15] Xu Y.Z., Lei P., Fei Y. A., Hou Y., Chen G. Z., Zhou Z. Q., Zou H. H., Wei H. B., Xie W. Q. Tetrahedron Lett. 2023, 114, 154261.

Communesin生物碱核心五环骨架的高效合成

Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Longlong Li, Xinyue He, Longsheng Zhou, Hengtong Qu, Chengtao Feng, Kun Xu. NH₄SCN-Promoted Formal [3＋3] Annulation for the Synthesis of 5-Arylated Pyrazolo[1,5-a]pyrimidines [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2832-2840.
[2]	Yunxin Xing, Denghong Yan, Shun Wen, Jie Bu, Kun Shen. Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1938-1948.
[3]	Jiasheng Wang, Zeshu Wang, Weimin He, Longwu Ye. Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1786-1792.
[4]	Chenguang Liu. Progress in Asymmetric Hydrogenation of Aromatic N-Heterocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1403-1422.
[5]	Chun Gao, Xin Liu, Minghui Wang, Shuxian Liu, Tingting Zhu, Yikang Zhang, Erjun Hao, Qiliang Yang. Advances in Asymmetric Electrochemical Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 673-727.
[6]	Fan Yang, Ting Fang, Guichun Yang, Meng Gao. Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles [J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 1021-1030.
[7]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[8]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[9]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[10]	Sijie Fan, Wuheng Dong, Caiyun Liang, Guichao Wang, Yao Yuan, Zuodong Yin, Zhaoguo Zhang. Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3277-3286.
[11]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[12]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[13]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[14]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[15]	Wenlong Chen, Huimin Li, Pengfei Yang, Dongcheng Zheng, Gaosheng Yang. Reaction of 2-Aroylmethylenemalonates with Corey Ylide [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1472-1482.