Citation: Su Yingpeng, Feng Yawei, Cao Lindan, Xue Wenxuan, Shi Ya, Chang Bingbing, Huang Danfeng, Wang Ke-Hu, Hu Yulai. Triphenylphosphine Catalyzed Lu's[3+2] Annulation of Aurones and Alkenoates: Constructing of Spiro[1-benzofuran-3-one-2, 5'-cyclopentene] Polycyclic Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1333-1343. doi: 10.6023/cjoc201812022 shu

Triphenylphosphine Catalyzed Lu's[3+2] Annulation of Aurones and Alkenoates: Constructing of Spiro[1-benzofuran-3-one-2, 5'-cyclopentene] Polycyclic Compounds

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Su Yingpeng, suyp51@nwnu.edu.cn
Received Date: 12 December 2018
Revised Date: 13 February 2019
Available Online: 22 May 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21502154, 21362033) and the Gansu Provincial Science and Technology Program (No. 17JR5RA073)the National Natural Science Foundation of China 21362033the National Natural Science Foundation of China 21502154the Gansu Provincial Science and Technology Program 17JR5RA073

Figures(3)

The PPh₃ catalyzed Lu's[3+2] annulation of aurones with alkenoates has been developed to form spiro-[1-ben-zofuran-3-one-2, 5'-cyclopentene] polycyclic moiety. The usefulness of this strategy has been demonstrated by the use of a wide variety of substrates to give desired polycyclic compounds in high yield under mild and simple reaction condition. This methodology research offered a fine entry for synthesis of natural product applanatumin A and its analogues.
- aurones,
- alkenoate,
- PPh₃,
- Lu's[3+2] annulation
1. [1]
  (a) Luo, Q.; Di, L.; Dai, W.-F.; Lu, Q.; Yan, Y.-M.; Yang, Z.-L.; Li, R.-T.; Cheng, Y.-X. Org. Lett. 2015, 17, 1110.
  (b) Luo, Q.; Wei, X.-Y.; Yang, J.; Luo, J.-F.; Liang, R.; Tu, Z.-C.; Cheng, Y.-X. J. Nat. Prod. 2017, 80, 61.
  (c) Li, Q.-M.; Luo, J.-G.; Zhang, Y.-M.; Li, Z.-R.; Wang, X.-B.; Yang, M.-H.; Luo, J.; Sun, H.-B.; Chen, Y.-J.; Kong, L.-Y. Chem. Eur. J. 2015, 21, 13206.
2. [2]
  (a) Kaishap, P. P.; Duarah, G.; Sarma, B.; Chetia, D.; Gogoi, S. Angew. Chem., Int. Ed. 2018, 57, 456.
  (b) Ni, H.; Yu, Z.; Yao, W.; Lan, Y.; Ullah, N.; Lu, Y. Chem. Sci. 2017, 8, 5699.
3. [3]
  Kobayashi, S.; Jorgensen, K. A. Cycloaddition Reactions in Organic Synthesis, WILEY-VCH Verlag GmbH, Weinheim, 2002, pp. 5~327.
4. [4]
5. [5]
  Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. doi: 10.1021/jo00114a048
6. [6]
  (a) Fu, W.; Tang, W. ACS Catal. 2016, 6, 4814.
  (b) Gladiali, S.; Alberico, E.; Junge, K.; Beller, M. Chem. Soc. Rev. 2011, 40, 3744.
  (c) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
7. [7]
  (a) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426.
  (b) Xiao, H.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Angew. Chem., Int. Ed. 2010, 49, 4467.
  (c) Gicquel, M.; Zhang, Y.; Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2015, 54, 5470.
  (d) Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G.; Voituriez, A.; Marinetti, A. Chem.-Eur. J. 2010, 16, 1033.
  (e) Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti, A. Chem.-Eur. J. 2010, 16, 12541.
  (f) Lee, S. Y.; Fujiwara, Y.; Nishiguchi, A.; Kalek, M.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 4587.
8. [8]
  (a) Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074.
  (b) Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510.
  (c) Cai, L.; Zhang, K.; Kwon, O. J. Am. Chem. Soc. 2016, 138, 3298.
9. [9]
10. [10]
  Hoffmann, M.; Miaskiewicz, S.; Weibel, J.-M.; Pale, P.; Blanc, A. RSC Adv. 2015, 5, 37138. doi: 10.1039/C5RA03228H
11. [11]
  Rout, L.; Harned, A. M. Chem.-Eur. J. 2009, 15, 12926. doi: 10.1002/chem.v15:47
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