An Improved Total Synthesis of Tubercidin

doi:10.6023/cjoc201402027

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1358-1363.DOI: 10.6023/cjoc201402027 Previous Articles Next Articles

ARTICLE

杀结核菌素的全合成研究

黄海洋, 阮志忠, 胡韬, 肖强

江西科技师范大学有机功能分子研究所南昌 330013

收稿日期:2014-02-23 修回日期:2014-03-20 发布日期:2014-04-10
通讯作者: 肖强 E-mail:xiaoqiang@tsinghua.org.cn
基金资助:
国家自然科学基金（Nos.20962009，21062006）、教育部新世纪优秀人才支持计划（No.11-1000）、江西省青年科学家培养对象项目和南昌市科技局资助项目.

An Improved Total Synthesis of Tubercidin

Huang Haiyang, Ruan Zhizhong, Hu Tao, Xiao Qiang

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013

Received:2014-02-23 Revised:2014-03-20 Published:2014-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20962009, 21062006), the Program for New Century Excellent Talents in University (No. 11-1000), the Training Project of Jiangxi Youth Scientists and the Bureau of Science & Technology of Nanchang City.

Tubercidin is a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside with significantly biological activities, such as anti-schistosomal, antibacterial and antitumor. An improved total synthesis of tubercidin is reported using microwave promoted Vorbrüggen glycosylation as the key step. Thus, tubercidin was synthesized in 3 steps with 74% overal yield using 6-chloro-7-bromo-pyrrolo[2,3-d]pyrimidine and 1-O-acetyl-2,3,5-O-tribenzoyl-β-D-ribose as starting materials. The applica- tion of micromave irridated one-pot reaction is also reported in the synthesis of 7-deazapurine nucleosides using potassium nonafluoro-1-butanesulfonate, trimethylsilyl chloride and silylation reagent [hexamethyldisilazane or N,O-bis(trimethyl- silyl)acetamide].

Key words: nucleoside, total synthesis, natural product, glycosylation, microwave

Cite this article

Huang Haiyang, Ruan Zhizhong, Hu Tao, Xiao Qiang. An Improved Total Synthesis of Tubercidin[J]. Chin. J. Org. Chem., 2014, 34(7): 1358-1363.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Anzai, K.; Nakamura, G.; Suzuki, S. J. Antibiot., Ser. A 1957, 10, 201.

(b) Acs, G.; Reich, E.; Mori, M. Proc. Natl. Acad. Sci. U. S. A. 1964, 52, 493.

[2] (a) Jaffe, J. J.; Meymarian, E.; Doremus, H. M. Nature 1971, 230, 408.

(b) Jaffe, J. J.; Doremus, H. M.; Dunsford, H. A.; Kammerer, W. S.; Meymarian, E. Am. J. Trop. Med. Hyg. 1973, 22, 62.

[3] Bloch, A.; Leonard, R. J.; Nichol, C. A. Biochim. Biophys. Acta, Nucleic Acids Protein Synth. 1967, 138, 10.

[4] Miko, M.; Drobnica, L. Experientia 1975, 31, 832.

[5] Seibert, G.; Maidhof, A.; Zahn, R. K.; Muller, W. E. Gann 1978, 69, 739.

[6] (a) Smith, C. G.; Reineke, L. M.; Burch, M. R.; Shefner, A. M.; Muirhead, E. E. Cancer Res. 1970, 30, 69.

(b) Grage, T. B.; Rochlin, D. B.; Weiss, A. J.; Wilson, W. L. Cancer Res. 1970, 30, 79.

(c) Bisel, H. F.; Ansfield, F. J.; Mason, J. H.; Wilson, W. L. Cancer Res. 1970, 30, 76.

[7] Mooberry, S. L.; Stratman, K.; Moore, R. E. Cancer Lett. 1995, 96, 261.

[8] (a) Zhang, X.; Jia, D.; Liu, H.; Zhu, N.; Zhang, W.; Feng, J.; Yin, J.; Hao, B.; Cui, D.; Deng, Y.; Xie, D.; He, L.; Li, B. PLoS One 2013, 8, e62527.

(b) Ugarkar, B. G.; DaRe, J. M.; Kopcho, J. J.; Browne, C. E.; Schanzer, J. M.; Wiesner, J. B.; Erion, M. D. J. Med. Chem. 2000, 43, 2883.

[9] (a) Sun, J.; Dou, Y.; Ding, H.; Yang, R.; Sun, Q.; Xiao, Q. Mar. Drugs 2012, 10, 881.

(b) Dou, Y.-H.; Ding, H.-X.; Yang, R.-C.; Li, W.; Xiao, Q. Chin. Chem. Lett. 2013, 24, 379.

(c) Li, Q. H.; Yang, R. C.; Ruan, Z. Z; Hu, T.; Ding, H. X.; Xiao, Q. Chin. J. Org. Chem. 2013, 33, 1340 (in Chinese).

(李启欢, 阳如春, 阮志忠, 胡韬, 丁海新, 肖强, 有机化学, 2013, 33, 1340.)

(d) Ding, H. X.; Da, L. C.; Yang, R. C.; Cao, B. P.; Sun, Q.; Xiao, Q. Chin. Chem. Lett. 2012, 23, 996.

(e) Cao, B.; Ding, H.; Yang, R.; Wang, X.; Xiao, Q. Mar. Drugs 2012, 10, 1412.

(f) Song, Y.; Ding, H.; Dou, Y.; Yang, R.; Sun, Q.; Xiao, Q.; Ju, Y. Synthesis 2011, 1442.

[10] (a) Kazimierczuk, Z.; Revankar, G. R.; Robins, R. K. Nucleic Acids Res. 1984, 12, 1179.

(b) Ramasamy, K.; Imamura, N.; Robins, R. K.; Revankar, G. R. J. Heterocycl. Chem. 1988, 25, 1893.

(c) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670.

(d) Seela, F.; Westermann, B.; Bindig, U. J. Chem. Soc., Perkin Trans. 1 1988, 697.

(e) Rosemeyer, H.; Seela, F. Helv. Chim. Acta 1988, 71, 1573.

(f) Seela, F.; Kretschmer, U. J. Heterocycl. Chem. 1990, 27, 479.

(g) Seela, F.; Soulimane, T.; Mersmann, K.; Jürgens, T. Helv. Chim. Acta 1990, 73, 1879.

[11] Ramasamy, K.; Imamura, N.; Robins, R. K.; Revankar, G. R. Tetrahedron Lett. 1987, 28, 5107.

[12] (a) Tolman, R. L.; Robins, R. K.; Townsend, L. B. J. Am. Chem. Soc. 1968, 90, 524.

(b) Tolman, R. L.; Robins, R. K.; Townsend, L. B. J. Am. Chem. Soc. 1969, 91, 2102.

(c) Kondo, T.; Ohgi, T.; Goto, T. Agric. Biol. Chem. 1977, 41, 1501.

[13] (a) Niedballa, U.; Vorbruggen, H. J. Org. Chem. 1976, 41, 2084.

(b) Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.

(c) Teng, K.; Cook, P. D. J. Org. Chem. 1994, 59, 278.

(d) Zhong, M. H.; Robins, M. J. Tetrahedron Lett. 2003, 44, 9327.

(d) Spadafora, M.; Mehiri, M.; Burger, A.; Benhida, R. Tetrahedron Lett. 2008, 49, 3967.

(e) Vorbrüggen, H.; Ruh-Pohlenz, C. Handbook of Nucleoside Synthesis, John Wiley & Sons, New York, 2001.

[14] Bio, M. M.; Xu, F.; Waters, M.; Williams, J. M.; Savary, K. A.; Cowden, C. J.; Yang, C.; Buck, E.; Song, Z. J.; Tschaen, D. M.; Volante, R. P.; Reamer, R. A.; Grabowski, E. J. J. J. Org. Chem. 2004, 69, 6257.

[15] (a) Seela, F.; Peng, X. H. J. Org. Chem. 2006, 71, 81.

(b) Seela, F.; Ming, X. Tetrahedron 2007, 63, 9850.

(c) Peng, X. H.; Seela, F. Nucleosides, Nucleotides Nucleic Acids 2007, 26, 603.

[16] (a) Dillon, M. P.; Bois, D. J. D.; Lai, Y. J.; Hawley, R. C.; Wang, B. H. WO 2010066629, 2010[Chem. Abstr. 2010, 153, 37183].

(b) Nichols, P. L.; Sehmi, S. S.; Ward, R. W.; Wilson, D. M. WO 2009080682, 2009[Chem. Abstr. 2009, 151, 124018].

[17] (a) Xiao, S. Y.; Zhu, J.; Mu, X. J.; Li, Z. H. Chin. J. Org. Chem. 2013, 33, 1668 (in Chinese).

(肖尚友, 朱俊, 穆小静, 李正华, 有机化学, 2013, 33, 1668.)

(b) Takkellapati, S. R. Curr. Org. Chem. 2013, 17, 2305.

[18] Bookser, B. C.; Raffaele, N. B. J. Org. Chem. 2007, 72, 173.

[19] (a) Chen, B. H.; Li, J. T.; Lan, R. J. Chin. J. Org. Chem. 2013, 33, 1965 (in Chinese).

(陈保华, 李记太, 兰瑞家, 陈国锋, 有机化学, 2013, 33, 1965.)

(b) Baig, N. B. R.; Varma, R. S. Curr. Org. Chem. 2013, 17, 2323.

[20] (a) Vorbruggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279.

(b) Vorbrueggen, H. Helv. Chim. Acta 2011, 94, 947.

[21] Kim, J.; Pordesimo, E. O.; Toth, S. I.; Schmitz, F. J.; van Altena, I. J. Nat. Prod. 1993, 56, 1813.

[22] Anderson, J. D.; Bontems, R.; Geary J. S.; Cottam, H. B.; Larson, S. B.; Matsumoto, S. S.; Smee, D. F.; Robins, R. K. Nucleosides Nucleotides 1989, 8, 1201.

[23] Moreau, C.; Wagner, G. K.; Weber, K.; Guse, A. H.; Potter, B. V. L. J. Med. Chem. 2006, 49, 5162.

杀结核菌素的全合成研究

An Improved Total Synthesis of Tubercidin

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[2]	Chuantao Zhu, Song Wang, Yifan Zhao, Piet Herdewijn, Fengwu Liu. Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3167-3173.
[3]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[4]	Xiurong Wu, Chaojiang Xiao, Yi Shen, Hongxia Tang, Junyi Zhu, Bei Jiang. Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022 [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2764-2789.
[5]	Fei Wang, Wenbing Jin, Xianfeng Hou, Gongli Tang, Haixue Pan. In vivo Studies on the Biosynthetic Pathway of Aureonuclemycin and Identification of Key Metabolites [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2561-2566.
[6]	Gefei Li, Jie Jing, Zhenyang Luo, Juan Mo, Decai Xiong, Xinshan Ye. Recent Advances in Protection-Free Glycosylations [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1991-2001.
[7]	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.
[8]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[9]	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.
[10]	Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.
[11]	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.
[12]	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.
[13]	Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao, Nianyu Huang. Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2140-2154.
[14]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[15]	Mengnan Lai, Qiuyuan Wang, Min Hua, Nianyu Huang, Hui Yao. Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1694-1705.