Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation

doi:10.6023/A1111101

Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (12): 1367-1370.DOI: 10.6023/A1111101 Previous Articles Next Articles

Special Topic

金催化分子间氧化炔合成5-(3-吲哚基)-噁唑天然产物

吴运东^a, 彭莎^a, 欧阳跃军^b, 钱鹏程^a, 何卫民^a, 向建南^a

a 湖南大学化学生物传感与计量学国家重点实验室湖南大学化学化工学院长沙 410082;
b 怀化学院化学化工系怀化 418000

投稿日期:2011-11-10 修回日期:2012-04-19 发布日期:2012-04-20
通讯作者: 何卫民, 向建南 E-mail:jnxiang@hnu.cn, wmhe82@hotmail.com
基金资助:
湖南省科技厅重点项目(No. 2009WK4005)、湖南省自然科学基金(No. 11JJ5008)和长沙市科技局重点项目(No. K082152-31)资助项目.

Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation

Wu Yundong^a, Peng Sha^a, Ouyang Yuejun^b, Qian Pengcheng^a, He Weimin^a, Xiang Jiannan^a

a State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University and College of Chemistry and Chemical Engineering, Changsha 410082;
b Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418000

Received:2011-11-10 Revised:2012-04-19 Published:2012-04-20
Supported by:
Project supported by Department of Science and Technology Foundation of Hunan Province (No. 2009WK4005), Hunan Natural Science Foundation (No. 11JJ5008) and Changsha Science and Technology (No. K082152-31).

The recent development of new gold(I) catalytic methods has opened the door to the total synthesis of natural products and bioactive complex molecules. We describe a convenient, straightforward, efficient and environmentally benign protocol to synthesize the 5-(3-indolyl)oxazole. The new synthetic route was finished in five steps including iodization, N-Boc protection, Sonogashira cross-coupling, gold catalyzed reaction, deprotection using indole as the starting material. The key step was generation of α-oxo carbene via gold-catalyzed intermolecular oxidation of alkynes (2).

Key words: gold-catalysis, 8-methylquinoline N-oxide, α-oxo gold carbene, oxazole, indole

Cite this article

Wu Yundong, Peng Sha, Ouyang Yuejun, Qian Pengcheng, He Weimin, Xiang Jiannan. Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation[J]. Acta Chimica Sinica, 2012, 70(12): 1367-1370.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Narasimhan, M. J.; Ganla, V. G. Hind. Antibiot. Bull. 1967, 9, 138.

2 Koyama, Y.; Yokose, K.; Dolby, L. J. Agric. Biol. Chem. 1981, 45, 1285.

3 Takeuchi, T.; Ogawa, K.; Iinuma, H.; Suda, H.; Ukita, K. J. Antibiot. 1973, 26, 162.

4 Naik, S. R.; Harindran, J.; Varde, A. B. J. Biotechnol. 2001, 88, 1.

5 Noltemeyer, M.; Sheldrick, G. M.; Hoppe, H. U.; Zeeck, A. J. Antibiot. 1982, 35, 549.

6 Bhate, D. S.; Hulyalkar, R. K.; Menon, S. K. Experientia 1960, 16, 504.

7 Umehara, K.; Yoshida, K.; Okamoto, M.; Iwami, M.; Tanaka, H.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1984, 37, 1153.

8 Pettit, G. R.; Knight, J. C.; Delbert, L.; Davenport, R.; Pettit, R. K.; Tucker, B. E.; Schmidt, J. M. J. Nat. Prod. 2002, 65, 1793.

9 Oikawa, Y.; Yoshida, T.; Mohri, K.; Yonemitsu, O. Heterocycles 1979, 12, 1457.

10 Molina, P.; Fresneda, P. M.; Almendros, P. Synthesis 1993, 54.

11 Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021.

12 Kumar, D.; Sundaree, S.; Patel, G.; Rao, V. S. Tetrahedron Lett. 2008, 49, 867.

13 Miyake, F.; Hashimoto, M.; Tonsiengsom, S.; Yakushijin, K.; Horne, D. A. Tetrahedron 2010, 66, 4888.

14 Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745.

15 Joshi, B. S.; Taylor, W. I.; Bhate, D. S.; Karmarkar, S. S. Tetrahedron 1963, 19, 1437.

16 Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536.

17 Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994.

18 Zhang, L.; Wang, S.; Zhang, G. Synlett 2010, 692.

19 Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766.

20 Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226.

21 Ye, L.; He, W.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 3236.

22 Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550.

23 Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258.

24 Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738.

25 Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070.

26 Qian, D.; Zhang, J. Chem. Commun. 2011, 47, 11152.

27 Qi, C.; Jiang, H.; Huang, L.; Yuan, G.; Ren, Y. Org. Lett. 2011, 13, 5520.

28 Huang, H.; Zhou, Y.; Liu, H. Beilstein J. Org. Chem. 2011, 7, 897.

29 Chen, D.; Song, G.; Jia, A.; Li, X. J. Org. Chem. 2011, 76, 8488.

30 He, W.; Xie, L.; Xu, Y.; Xiang, J.; Zhang, L. Org. Biomol. Chem. 2012, 10, 3168.

31 He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 133, 8482.

32 Berg, M.; Bal, G.; Goeminne, A.; Van?der?Veken, P.; Versées, W.; Steyaert, J.; Haemers, A.; Augustyns, K. ChemMedChem 2009, 4, 249.

33 Mothes, C. L.; Lavielle, S.; Karoyan, P. J. Org. Chem. 2008, 73, 6706. Benhida, R.; Blanchard, P.; Fourrey, J.-L. Tetrahedron Lett. 1998, 39, 6849.

[1]	Weiyang Gao, Weichao Deng, Yang Gao, Renxiao Liang, Yixia Jia. Intermolecular Enantioselective Dearomative Oxidative Heck Reaction of Indoles [J]. Acta Chimica Sinica, 2024, 82(1): 1-4.
[2]	Mengmeng Wang, Jun Zhang, Huiying Wang, Biao Ma, Hui-Xiong Dai. Construction of Aza-spiro[4,5]indole Scaffolds via Rhodium-Catalyzed Regioselective C(4)—H Activation of Indole^※ [J]. Acta Chimica Sinica, 2022, 80(3): 277-281.
[3]	Long Zheng, Lijia Wang, Yong Tang. Intramolecular Ring-opening of Indole-cyclopropanes^※ [J]. Acta Chimica Sinica, 2022, 80(3): 255-258.
[4]	Linjun Zhan, Wei Hu, Mei Wang, Bin Huang, Ya-Qiu Long. Imidoyl Chloride Mediated One-Pot Synthesis of 3-Electron Withdrawing Group Substituted Indoles [J]. Acta Chimica Sinica, 2021, 79(7): 903-907.
[5]	Bo Zhou, Renxiao Liang, Zhongyan Cao, Pinghai Zhou, Yixia Jia. Palladium-Catalyzed Heck Reaction of Endocyclic Conjugated C=C Bonds of Pyrroles [J]. Acta Chimica Sinica, 2021, 79(2): 176-179.
[6]	Huang Hao, Lin Huaxin, Wang Min, Liao Jian. Copper-Catalyzed Enantioselective Aminoboration of Styrenes with 1,2-Benzisoxazole as Nitrogen Source [J]. Acta Chimica Sinica, 2020, 78(11): 1229-1234.
[7]	Zhang Shuo, Hou Zitong, Song Zihe, Su Xiaofeng, Wang Feng, Yu Yitao, Peng Dan, Cui Shiqi, Liu Yifan, Wang Jiarui, Song Jianjun. Zn/Ni Bimetallic Relay Catalysis: One Pot Intramolecular Cycloisomerization/Intermolecular Amidoalkylation Reaction toward Oxazole Derivatives [J]. Acta Chimica Sinica, 2019, 77(11): 1168-1172.
[8]	Ren Zhiwen, Ren Nan, Zhang Faguang, Ma Junan. Facile Synthesis of Fluorinated Isoxazoles via Consecutive Double C—F Bond Cleavage [J]. Acta Chim. Sinica, 2018, 76(12): 940-944.
[9]	Liao Fumin, Du Yi, Zhou Feng, Zhou Jian. Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles [J]. Acta Chim. Sinica, 2018, 76(11): 862-868.
[10]	Yan Wen-Guang, Wang Pan, Wang Lijia, Sun Xiu-Li, Tang Yong. Copper Catalyzed[3+2] Annulation of Indoles with 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes [J]. Acta Chim. Sinica, 2017, 75(8): 783-787.
[11]	Zhang Ling, Zhang Peizhi, Xue Jianfei, Sun Wangbin, Zou Jianping. Manganese Acetate-Mediated Phosphorylation of Indoles [J]. Acta Chim. Sinica, 2016, 74(10): 811-818.
[12]	Yin Xiaoping, Xu Pengwei, Dong Kun, Liao Kui, Zhou Feng, Zhou Jian. Ga(OTf)₃ Catalyzed Highly Efficient Substitution Reaction of 3-Hydroxyoxindoles Using TMSN₃ [J]. Acta Chim. Sinica, 2015, 73(7): 685-689.
[13]	Duan Dehe, Yin Qin, Wang Shouguo, Gu Qing, You Shuli. Chiral Phosphoric Acid-Catalyzed Asymmetric Cascade Reaction of C(3) Substituted Indoles and Methyl Vinyl Ketone [J]. Acta Chim. Sinica, 2014, 72(9): 1001-1004.
[14]	Wang Yuhui, Cao Zhongyan, Niu Yanfei, Zhao Xiaoli, Zhou Jian. Highly Enantioselective Organocatalytic aza-Henry Reaction of Nitroalkanes to N-Boc Isatin Ketimines [J]. Acta Chimica Sinica, 2014, 72(7): 867-872.
[15]	Chu Ningning, Feng Chengliang, Ji Min. Advances in Applications of Fluorescent Probes Based on Indole Heptamethine in Vivo [J]. Acta Chimica Sinica, 2013, 71(11): 1459-1476.

金催化分子间氧化炔合成5-(3-吲哚基)-噁唑天然产物

Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments