Citation: Wang Qi, Zhang Chao, Yang Jun. Synthesis of ACE tricyclic systems of daphnicyclidin A and dehy-droxymacropodumine A[J]. Chinese Chemical Letters, ;2020, 31(7): 1906-1910. doi: 10.1016/j.cclet.2019.12.018 shu

Synthesis of ACE tricyclic systems of daphnicyclidin A and dehy-droxymacropodumine A

Wang Qi ¹ ,
Zhang Chao ¹ ,
Yang Jun ^*,

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Chang'an Campus, Xi'an 710119, China

junyang@snnu.edu.cn

Received Date: 16 November 2019
Revised Date: 5 December 2019
Accepted Date: 11 December 2019
Available Online: 14 December 2019

Figures(6)

The synthesis of the ACE tricyclic system ofdaphnicyclidin A and dehydroxymacropodumine A are developed. The key reactions include an efficient aldol reaction to introduce chiral fragment 33 for further construction of piperidine ring B and seven -membered ring C, a nucleophilic addition of lithium pentene to aldehyde for installation of ring E, and a photocatalytic decarboxylation conjugate addition to construct ring C.
- Tricyclic system,
- Daphnicyclidin A,
- Dehydroxymacropodumine A,
- Photocatalytic decarboxylation,
- Conjugate addition
1. [1]
  (a) A.K. Chattopadhyay, S. Hanessian, Chem. Rev. 117 (2017) 4104-4146;
  (b) H.F. Wu, X.P. Zhang, L.S. Ding, et al., Planta Med. 79 (2013) 1589-1598;
  (c) J. Kobayashi, T. Kubota, Nat. Prod. Rep. 26 (2009) 936-962.
2. [2]
  (a) H. Morita, J. Kobayashi, Org. Lett. 5 (2003) 2895-2898;
  (b) H. Zhang, S.P. Yang, C.Q. Fan, J. Ding, J.M. Yue, J. Nat. Prod. 69 (2006) 553-557;
  (c) S.P. Yang, H. Zhang, C. Zhang, J.M. Yue, J. Nat. Prod. 69 (2006) 79-82;
  (d) S.Z. Mu, C.S. Li, H.P. He, J. Nat. Prod. 70 (2007) 1628-1631;
  (e) Q. Zhang, Y.T. Di, C.S. Li, Org. Lett. 11 (2009) 2357-2359;
  (f) H. Zhang, S.L. Shyaula, J.Y. Li, J. Nat. Prod. 78 (2015) 2761-2767;
  (g) H. Zhang, S.L. Shyaula, J.Y. Li, Org. Lett. 18 (2016) 1202-1205.
3. [3]
  (a) H. Morita, N. Yoshida, J. Kobayashi, J. Org. Chem. 67 (2002) 2278-2282;
  (b) S.P. Yang, J.M. Yue, Org. Lett. 6 (2004) 1401-1404;
  (c) M.M. Cao, H.P. He, Y.C. Gu, Nat. Prod. Bioprospect. 3 (2013) 29-32;
  (d) Y. Lu, K. Gao, X. Wang, Molecules 19 (2014) 3055-3067.
4. [4]
  (a) Z.Y. Li, P. Chen, H.G. Xu, et al., Chin. J. Chem. 26 (2008) 348-352;
  (b) W. Zhang, Y.W. Guo, K. Krohn, Chem.-Eur. J. 12 (2006) 5122-5127.
5. [5]
  (a) C.H. Heathcock, Proc. Natl. Acad. Sci. U. S. A. 93 (1996) 14323-14327;
  (b) Y. Inaba, H. Morita, J. Kobayashi, J. Am. Chem. Soc.123 (2001) 11402-11408;
  (c) H. Morita, J. Kobayashi, Tetrahedron 58 (2002) 6637-6641;
  (d) Y.T. Di, X.J. Hao, J. Nat. Prod. 82 (2019) 427-430.
6. [6]
  (a) H. Zhang, S.P. Yang, C.Q. Fan, J. Ding, J.M. Yue, J. Nat. Prod. 69 (2006) 553-557;
  (b) C.R. Zhang, H.B. Liu, T. Feng, et al., J. Nat. Prod. 72 (2009) 1669-1672;
  (c) S. Liu, J.H. Zhang, Y.T. Di, J.Y. Dong, X.J. Hao, Nat. Prod. Res. 32 (2018) 2165-2170;
  (d) J.B. Xu, H. Zhang, L.S. Gan, et al., J. Am. Chem. Soc. 136 (2014) 7631-7633;
  (e) H. Morita, N. Ishioka, H. Takatsu, et al., Org. Lett. 7 (2005) 459-462;
  (f) S. Saito, H. Yahata, T. Kubota, et al., Tetrahedron 64 (2008) 1901-1908.
7. [7]
  (a) Z. Lu, Y. Li, J. Deng, A. Li, Nat. Chem. 5 (2013) 679;
  (b) J. Li, W. Zhang, F. Zhang, A. Li, J. Am. Chem. Soc. 139 (2017) 14893-14896;
  (c) Y. Chen, W. Zhang, L. Ren, A. Li, Angew. Chem. Int. Ed. 57 (2018) 952-956;
  (d) H. Shi, I.N. Michaelides, B. Darses, D. Darren, J. Am. Chem. Soc. 139 (2017)17755-17758;
  (e) X. Chen, H.J. Zhang, X. Yang, H.B. Zhai, Angew. Chem. Int. Ed. 130 (2018)959-963;
  (f) W. Zhang, M. Ding, J. Li, A. Li, J. Am. Chem. Soc. 140 (2018) 4227-4231;
  (g) H.Y. Sun, G.M. Wu, X.G. Xi, Chin. Chem. Lett. 30 (2019) 1538-1540;
  (h) H.J. Wang, Q.Y. Dong, Q.X. Xie, P. Tang, Chin. Chem. Lett. 31 (2019) 685-688.
8. [8]
  (a) S. Ikeda, M. Shibuya, N. Kanoh, Y. Iwabuchi, Org. Lett. 11 (2009) 1833-1836;
  (b) T.B. Dunn, J.M. Ellis, C.C. Kofink, L.E. Overman, Org. Lett. 11 (2009) 5658-5661;
  (c) D.R. Williams, P.K. Mondal, S.A. Bawel, Org. Lett. 16 (2014) 1956-1959;
  (d) J.L. Li, H.W. Shi, Q. Wang, J. Yang, Org. Lett. 19 (2017) 1497-1499.
9. [9]
  (a) O. Chisa, W.C. David, MacMillan, J. Am. Chem. Soc.136 (2014) 10886-10889;
  (b) M.J. Schnermann, L.E. Overman, Angew. Chem. Int. Ed. 51 (2012) 9576-9580;
  (c) J.T. Daniel, S. Yuriy, M. Mikko, L.E. Overman, J. Am. Chem. Soc. 140 (2018)3091-3102;
  (d) Y. Ouyang, Y. Peng, W.D.Z. Li, Tetrahedron 75 (2019) 4486-4496.
10. [10]
  (a) A. Nakazaki, T. Era, Y. Numada, Tetrahedron 62 (2006) 6264-6271;
  (b) H. Yu, T. Gai, W.L. Sun, M.S. Zhang, Chin. Chem. Lett. 22 (2011) 379-381;
  (c) M. Gao, Y.C. Wang, Z.H. Yao, Angew. Chem. Int. Ed. 57 (2018) 13313-13318.
11. [11]
  (a) E.J. Corey, K.C. Nicolaou, J. Am. Chem. Soc. 96 (1974) 5614-5616;
  (b) M.B. Andrus, T.L. Shih, J. Org. Chem. 61 (1996) 8780-8785;
  (c) X.M. Zhu, L.L. He, G.L. Yang, et al., Synlett. (2006) 3510-3512;(d) R.G. Ren, J.Y. Ma, Z.Y. Mao, Y.W. Liu, B.G. Wei, Chin. Chem. Lett. 26 (2015)1209-1215.
12. [12]
  (a) D.H.R. Barton, S.W. McCombie, J. Chem. Soc. 1 (1975) 1574-1585;
  (b) H. Deng, X. Yang, Z. Tong, Z. Li, H. Zhai, Org. Lett. 10 (2008) 1791-1793;
  (c) Z.H. Zhao, A. Wang, P.S. Lei, Chin. Chem. Lett. 30 (2019) 425-427.
13. [13]
  (a) Y.H. Wan, A. Shaik, K. Chen, Chem. Rec. 17 (2017) 363-381;
  (b) D. Daniel, R. Oliver, J. Org. Chem. 81 (2016) 10357-10365;
  (c) H.Y. Duan, J. Ma, Z.Z. Yuan, F. Xu, Chin. Chem. Lett. 26 (2015) 646-648.
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