Citation: Yu Jieqiang, Jia Jun, Wang Xingwang. Synthesis of a Type of Linear β, γ-Unsaturated α-Keto Tryptophol Ester Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2778-2787. doi: 10.6023/cjoc202005051 shu

Synthesis of a Type of Linear β, γ-Unsaturated α-Keto Tryptophol Ester Compounds

Yu Jieqiang ^a ,
Jia Jun ^b,, ,
Wang Xingwang ^a,,

a.
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
b.
Analysis and Testing Center, Soochow University, Suzhou, Jiangsu 215123

Corresponding author: Jia Jun, jiajun@suda.edu.cn Wang Xingwang, wangxw@suda.edu.cn
Received Date: 19 May 2020
Revised Date: 22 June 2020
Available Online: 8 July 2020
Fund Project: the National Natural Science Foundation of China 21971176Project supported by the National Natural Science Foundation of China (No. 21971176)

Figures(1)

Tryptophol derivatives are very important compounds with wide spectrum of pharmaceutical and physiological activity. Herein, the esterification reaction of trypthol and its derivatives with β, γ-unsaturated α-keto acids was reported by the use of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole (HOBt) as conden-sation reagents. A series of β, γ-unsaturated α-keto trypanol ester derivatives were prepared in moderate to high yields. This method has advantages of riched functional group tolerance, readily available starting materials and easy operation.
- condensation reagent,
- tryptophol,
- esterification,
- β, γ-unsaturated α-keto acid,
- β, γ-unsaturated α-keto trypanol ester
1. [1]
  Emerit, M. B.; Riad, M.; Fattaccini, C. M.; Hamon, M. J. Neurochem. 1993, 60, 2059. doi: 10.1111/j.1471-4159.1993.tb03490.x
2. [2]
  (a) López-Noguera, S.; Petri, C.; Alburquerque, N.; Egea, J.; Burgos, L. Plant Sci. 2008, 175, 777.
  (b) Iqbal, N.; Trivellini, A.; Masood, A.; Ferrante, A.; Petri, N. A. Plant Physiol. Biochem. 2013, 73, 128.
  (c) Nongmaithem, S.; Devulapalli, S.; Sreelakshmi, Y.; Sharma, R. Plant Sci. 2020, 291, 110358.
  (d) Zhou, W. G.; Chen, F.; Meng, Y. J.; Chandrasekaran, U.; Luo, X. F. Plant Physiol. Biochem. 2020, 148, 228.
3. [3]
  (a) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942.
  (b) Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am. Chem. Soc. 2006, 128, 1424.
  (c) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
  (d) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190.
  (e) Trost, B. M.; Osipov, M.; Dong, G. B. J. Am. Chem. Soc. 2010, 132, 15800.
  (f) Cai, Q.; Liang, X.-W.; Wang, S.-G.; Zhang, J.-W.; Zhang, X.; You, S.-L. Org. Lett. 2012, 14, 5022.
4. [4]
  Palmieri, A.; Petrini, M. Nat. Prod. Rep. 2019, 36, 490. doi: 10.1039/C8NP00032H
5. [5]
  (a) Kong, S. J.; Zhang, J. B.; Li, X.; Pan. H.; Guo, D. Y. Biochem. Eng. J. 2020, 154, 107432.
  (b) Comaia, S.; Bertazzo, A.; Brughera, M.; Crotti. S. Adv. Clin. Chem. 2020, 95, 107432.
6. [6]
  Zheng, C.; You, S.-L. Nat. Prod. Rep. 2019, 36, 1589. doi: 10.1039/C8NP00098K
7. [7]
  Wu, Q.-F.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2012, 124, 1712. doi: 10.1002/ange.201107677
8. [8]
  Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558. doi: 10.1021/ar500167f
9. [9]
  Wu, Q.-F.; Zheng, C.; Zhuo, C.-X.; You, S.-L. Chem. Sci. 2016, 7, 4453. doi: 10.1039/C6SC00176A
10. [10]
  Zhou, Y.; Xia, Z.-L.; Gu, Q.; You, S.-L. Org. Lett. 2017, 19, 762. doi: 10.1021/acs.orglett.6b03610
11. [11]
  Li, J.-X.; Chen, G.-H.; Webster, J. M. Bioorg. Med. Chem. Lett. 1997, 7, 1349. doi: 10.1016/S0960-894X(97)00223-0
12. [12]
  (a) Yamamoto, Y. J. Org. Chem. 1986, 51, 886.
  (b) Fan, Y.-S.; Jiang, Y.-J.; An, D.; Sha, D.; Antilla, J. C.; Zhang, S. Q. Org. Lett. 2014, 16, 6112.
  (c) Schieferdecker, S.; Shabuer, G.; Letzel, A.-C.; Urbansky, B.; Ishida-Ito, M.; Ishida, K.; Cyrulies, M.; Dahse, H.-M.; Pidot, S.; Hertweck, C. ACS Chem. Biol. 2019, 14, 1490.
  (d) Zhang, Y.-S.; Gui, H.-Z.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2019, 7179.
  (e) Liu, Z.; Zhang, M.-Y.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2020, 1093.
13. [13]
  (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. J. Org. Chem. 1997, 62, 4721.
  (b) Santos, L. S.; Pilli, R. A.; Rawal, V. H. J. Org. Chem. 2004, 69, 1283.
  (c) Cheung, C.-M.; Goldberg, F. W.; Magnus, P.; Russell, C. J. J. Am. Chem. Soc. 2007, 129, 12320.
  (d) Santos, L. S.; Theoduloz, C.; Pilli, R. A.; Rodriguez, J. Eur. J. Med. Chem. 2009, 44, 3810.
  (e) Di Gioia, M. L.; Barattucci, A.; Bonaccorsi, P.; Leggio, A.; Minuti, L.; Romio, E.; Temperini, A.; Siciliano, C. RSC Adv. 2014, 4, 2678.
  (f) Dockendorff, C.; Wiedenhoeft, D.; Benoit, A.; Porter, J.; Wu, Y.; Virdi, R.; Shanaa, A. Synthesis 2016, 48, 2413.
  (g) Shelton, J.; Lu, X.; Hollenbaugh, J. A.; Cho, J. H.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2016, 116, 14379.
  (h) Shugrue, C. R.; Featherston, A. L.; Lackner, R. M.; Lin, A.; Miller, S. J. J. Org. Chem. 2018, 83, 4491.
14. [14]
  Du, Y.; Huang, H.-Y.; Liu, H.; Ruan, Y.-P.; Huang, P.-Q. Synlett 2011, 565.
15. [15]
  Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158. doi: 10.1039/c2ob26316e
16. [16]
  Han, L.; Liu, C.; Zhang, W.; Shi, X.-X.; You, S.-L. Chem. Commun. 2014, 50, 1231. doi: 10.1039/C3CC47921H
17. [17]
  Zhu, L.-F.; Meng, Q.-H.; Fan, W.-Z.; Xie, X.-M.; Zhang, Z.-G. J. Org. Chem. 2010, 75, 6027. doi: 10.1021/jo101084t
18. [18]
  Hua, Y.-Z.; Liu, M.-M.; Huang, P.-J.; Song, X.-X.; Wang, M.-C.; Chang, J.-B. Chem.-Eur. J. 2015, 21, 11994. doi: 10.1002/chem.201501655
19. [19]
  Cincinelli, R.; Scaglioni, L.; Arnold, N.-A.; Dallavalle, S. Tetrahedron Lett. 2011, 52, 5972. doi: 10.1016/j.tetlet.2011.08.143
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