Chinese Journal of Organic Chemistry >
Synthesis of Framework Structure of Guaiane
Received date: 2020-09-04
Revised date: 2020-11-09
Online published: 2020-12-05
A new method for the synthesis of chiral 5,7-fused oxygen bridged ring based on Prins cyclization is reported. It provides a new way for the synthesis of the skeleton structure of guaiacane sesquiterpenes. Based on dioxinone, the synthesis of chiral 5,7-fused oxygen bridged ring is achieved in a two-step combined yield of 72% by using Lewis acid induced intra- molecular Prins cyclization.
Result
Minshou Wang , Hongbin Zhang . Synthesis of Framework Structure of Guaiane[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1739 -1743 . DOI: 10.6023/cjoc202009010
| [1] | (a) Wang, J.; Chen, S.G.; Sun, B.F.; Lin, G.Q.; Shang, Y.J. Chemistry (Weinheim an der Bergstrasse, Germany) 2013, 19,2539. |
| [1] | (b) Wu, Y.B.; Ni, Z.Y.; Shi, Q.W.; Dong, M.; Kiyota, H.; Gu, Y.C.; Cong, B. Chem. Rev. 2012, 112,5967. |
| [1] | (c) Zhang, H.; Liu, H.B.; Yue, J.M. Chem. Rev. 2014, 114,883. |
| [1] | (d) Li, X.X.; Song, W.Z.; Ke, X.N.; Xu, X.F.; Liu, P.; Houk, K.N.; Zhao, X.L.; Tang, W.P. Chem.-Eur. J. 2016, 22,7079. |
| [1] | (e) Simeonov, S.P.; Nunes, J.P.; Guerra, K.; Kurteva, V.B.; Afonso, C.A. Chem. Rev. 2016, 116,5744. |
| [2] | (a) Akee, R.K.; Ransom, T.; Ratnayake, R.; McMahon, J.B.; Beutler, J.A. J. Nat. Prod. 2012, 75,459. |
| [2] | (b) Ratnayake, R.; Covell, D.; Ransom, T.T.; Gustafson, K.R.; Beutler, J.A. Org. Lett. 2009, 11,57. |
| [3] | (a) Miski, M.; Deluengo, D.H.; Mabry, T.J. Phytochemistry 1987, 26,199. |
| [3] | (b) Blanco, J.G.; Gil, R.R.; Alvarez, C.I.; Patrito, L.C.; GentiRaimondi, S.; Flury, A. FEBS Lett. 1997, 409,396. |
| [4] | (a) Hikino, H.; Ito, K.; Takemoto, T. Chem. Pharm. Bull. 1968, 16,1608. |
| [4] | (b) Yang, Y.; Kinoshita, K.; Koyama, K.; Takahashi, K.; Tai, T.; Nunoura, Y.; Watanabe, K. Phytomedicine 1999, 6,89. |
| [5] | (a) Rosselli, S.; Maggio, A.; Bellone, G.; Bruno, M. Tetrahedron Lett. 2006, 47,7047. |
| [5] | (b) Rasmussen, U.; Br?ogger Christensen, S.; Sandberg, F. Acta Pharm. Suec. 1978, 15,133. |
| [5] | (c) Huang, S.Z.; Zhang, X.; Ma, Q.Y.; Zheng, Y.T.; Dai, H.F.; Wang, Q.; Zhou, J.; Zhao, Y.X. RSC Adv. 2015, 5,80254. |
| [6] | Navickas, V.; Ushakov, D.B.; Maier, M.E.; Strobele, M.; Meyer, H.J. Org. Lett. 2010, 12,3418. |
| [7] | Hirose, T.; Miyakoshi, N.; Mukai, C. J. Org. Chem. 2008, 73,1061. |
| [8] | Jouanneau, M.; Bonepally, K.R.; Jeuken, A.; Tap, A.; Guillot, R.; Ardisson, J.; Ferezou, J.P.; Prunet, J. Org. Lett. 2018, 20,2176. |
| [9] | Li, W.; Liu, X.Z.; Zhou, X.F.; Lee, C.S. Org. Lett. 2010, 12,548. |
| [10] | Mascarenas, J.L.; Varela, I.; Lopez, F. Acc. Chem. Res. 2019, 52,465. |
| [11] | Parmar, D.; Matsubara, H.; Price, K.; Spain, M.; Procter, D.J. J. Am. Chem. Soc. 2012, 134,12751. |
| [12] | Nicolaou, K.C.; Kang, Q.A.; Ng, S.Y.; Chen, D.Y. K. J. Am. Chem. Soc. 2010, 132,8219. |
| [13] | Bao, W.L.; Tao, Y.Z.; Cheng, J.Q.; Huang, J.R.; Cao, J.M.; Zhang, M.X.; Ye, W.J.; Wang, B.; Li, Y.; Zhu, L.Z.; Lee, C.S. Org. Lett. 2018, 20,7912. |
| [14] | Li, G.J.; Xu, X.L.; Tian, H.C.; Liu, X.T.; Chen, W.; Yang, X.D.; Zhang, H.B. RSC Adv. 2017, 7,50822. |
| [15] | Han, Z.B.; Wang, Z.; Ding, K.L. Adv. Synth. Catal. 2011, 353,1584. |
| [16] | Chen, W.; Yang, X.D.; Tan, W.Y.; Zhang, X.Y.; Liao, X.L.; Zhang, H. Angew. Chem., Int. Ed. 2017, 56,12327. |
| [17] | Wang, M.S.; Wang, Z.; Chen, W.; Yang, X.D.; Zhang, H.B. Org. Lett. 2019, 21,1881. |
| [18] | Shen, Y.; Li, L.; Pan, Z.; Wang, Y.; Li, J.; Wang, K.; Wang, X.; Zhang, Y.; Hu, T.; Zhang, Y. Org. Lett. 2015, 17,5480. |
| [19] | (a) Krapcho, A.P. Synthesis-Stuttgart 1982,805. |
| [19] | (b) Krapcho, A.P. Synthesis-Stuttgart 1982,893. |
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