Citation: Ding Haixin, Li Chuang, Dong Xiangyou, Cao Banpen, Zhang Ning, Hong Sanguo, Xiao Qiang. First Total Synthesis of Marine Natural Nucleoside Kipukasin D[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3351-3355. doi: 10.6023/cjoc201806028 shu

First Total Synthesis of Marine Natural Nucleoside Kipukasin D

a.
Jiangxi Key Laboratory of Organi3 Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013
b.
Department of Chemistry, Nanchang University, Nanchang 330031

Corresponding author: Xiao Qiang, xiaoqiang@tsinghua.org.cn
Received Date: 19 June 2018
Revised Date: 11 July 2018
Available Online: 23 December 2018
Fund Project: the Bureau of Science & Technology of Jiangxi Province 20143ACB20012the Education Department of Jiangxi Province 170673Project supported by the National Natural Science Foundation of China (Nos. 21462019, 21676131), the Bureau of Science & Technology of Jiangxi Province (No. 20143ACB20012) and the Education Department of Jiangxi Province (No. 170673)the National Natural Science Foundation of China 21462019the National Natural Science Foundation of China 21676131

Figures(2)

The first total synthesis of marine natural nucleoside kipukasin D was disclosed in 9 steps and 15.7% overall yield using commercially available tetra-O-acetyl-β-D-ribose as starting material. In Vorbrüggen glycosylation, ortho-iodinebenzoate acted as neighboring participating group leading to β-nucleoside. The key step was selectively deprotection of 2'-O and 5'-O ortho-alkynylbenzoates by freshing prepared Ph₃PAuOTFA in the presence of ethanol (6 equiv.) and H₂O (1 equiv.) in dichloromethane (DCM). The reaction condition of our newly developed approach is very mild and neutral, which effectively avoids the transesterification between 2'-OH and 3'-OH. The result further demonstrat that ortho-alkynylbenzoate is an orthogonal protecting group compatible with other ester groups, which could find wide applications in nucleoside and carbohydrate chemistry.
- nucleoside,
- neighboring-group,
- transesterification,
- catalysis,
- total synthesis
1. [1]
  (a) Haefner, B. Drug Discovery Today 2003, 8, 536.
  (b) Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discov ery 2009, 8, 69.
2. [2]
3. [3]
  Sun, K.; Li, Y.; Guo, L.; Wang, Y.; Liu, P.; Zhu, W. Mar. Drugs 2014, 12, 3970. doi: 10.3390/md12073970
4. [4]
  Sugimoto, K.; Sadahiro, Y.; Kagiyama, I.; Kato, H.; Scherman, D. H.; Williams, R. M.; Tsukamoto, S. Tetrahedron Lett. 2017, 58, 2797. doi: 10.1016/j.tetlet.2017.05.057
5. [5]
  Wang, H.; Lu, Z.; Qu, H.; Liu, P.; Miao, C.; Zhu, T.; Li, J.; Hong, K.; Zhu, W. Arch. Pharmacal Res. 2012, 35, 1387. doi: 10.1007/s12272-012-0808-1
6. [6]
  Yang, G.; Sanjo, L.; Yun, K.; Leutou, A. S.; Kim, G. D.; Choi, H. D.; Kang, J. S.; Hong, J.; Son, B. W. Chem. Pharm. Bull. 2011, 59, 1174. doi: 10.1248/cpb.59.1174
7. [7]
  (a) Facey, P. C.; Porter, R. B.; Laatsch, H. Planta Med. 2016, 81, 1.
  (b) Liu, S.; Dai, H.; Konuklugil, B.; Orfali, R. S.; Lin, W.; Kalscheuer, R.; Proksch, P. Phytochem. Lett. 2016, 18, 187.
8. [8]
  Jiao, P.; Mudur, S. V.; Gloer, J. B.; Wicklow, D. T. J. Nat. Prod. 2007, 70, 1308. doi: 10.1021/np070241l
9. [9]
  Chen, M.; Fu, X. M.; Kong, C. J.; Wang, C. Y. Nat. Prod. Res. 2014, 28, 895. doi: 10.1080/14786419.2014.891114
10. [10]
  Zhuravleva, O. I.; Kirichuk, N. N.; Denisenko, V. A.; Dimtrenok, P. S.; Pivkin, M. V.; Afiyatullov, S. S. Chem. Nat. Compd. 2016, 52, 266. doi: 10.1007/s10600-016-1610-y
11. [11]
  (a) Cao, B.; Ding, H.; Yang, R.; Wang, X.; Xiao, Q. Mar. Drugs 2012, 10, 1412.
  (b) Sun, J.; Dou, Y.; Ding, H.; Yang, R.; Sun, Q.; Xiao, Q. Mar. Drugs 2012, 10, 881.
  (c) Hu, C.; Ruan, Z.; Ding, H.; Zhou, Y.; Xiao, Q. Molecules 2017, 22, 643.
12. [12]
13. [13]
  Li, C.; Ding, H.; Ruan, Z.; Zhou, Y.; Xiao, Q. Beilstein J. Org. Chem. 2017, 13, 855. doi: 10.3762/bjoc.13.86
14. [14]
  Jackson, M. D.; Denu, J. M. J. Biol. Chem. 2002, 277, 18535. doi: 10.1074/jbc.M200671200
15. [15]
  Dvorakova, M.; Pribylova, M.; Pohl, R.; Migaud, M. E.; Vanek, T. Tetrahedron 2012, 68, 6701. doi: 10.1016/j.tet.2012.05.117
16. [16]
  Hasegawa, H.; Akira, K.; Shinohara, Y.; Kasuya, Y.; Hashimoto, T. Biol. Pharm. Bull. 2001, 24, 852. doi: 10.1248/bpb.24.852
17. [17]
  Ding, H.; Li, C.; Zhou, Y.; Hong, S.; Zhang, N.; Xiao, Q. RSC Adv. 2017, 7, 1814. doi: 10.1039/C6RA27790J
1. [1]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
2. [2]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
3. [3]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
4. [4]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
5. [5]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
6. [6]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
7. [7]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
8. [8]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
9. [9]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
10. [10]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
11. [11]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
12. [12]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
13. [13]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
14. [14]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
15. [15]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
16. [16]
  Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
17. [17]
  Xue Liu , Lipeng Wang , Luling Li , Kai Wang , Wenju Liu , Biao Hu , Daofan Cao , Fenghao Jiang , Junguo Li , Ke Liu . Cu基和Pt基甲醇水蒸气重整制氢催化剂研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100049-. doi: 10.1016/j.actphy.2025.100049
18. [18]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
19. [19]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
20. [20]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1457)
HTML views(245)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142