Citation: Zhang Yana, Guo Liandong, Xu Jing. Efficient Synthesis of the AC Ring System of Daphnilactone B[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1079-1084. doi: 10.6023/cjoc201811017 shu

Efficient Synthesis of the AC Ring System of Daphnilactone B

Zhang Yana ^a,b ,
Guo Liandong ^b,, ,
Xu Jing ^b,,

a.
School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
b.
Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055

Corresponding author: Guo Liandong, guold@sustc.edu.cn Xu Jing, xuj@sustc.edu.cn
Received Date: 12 November 2018
Revised Date: 5 December 2018
Available Online: 21 April 2018
Fund Project: the Shenzhen Nobel Prize Scientists Laboratory Project C17783101the National Natural Science Foundation of China 21772082Project supported by the National Natural Science Foundation of China (No. 21772082), the Shenzhen Science and Technology Innovation Committee Basic Research Discipline Layout Project and Peacock Technology Innovation (Nos. JCYJ20170817110515599, KQJSCX2017072815423320), the Shenzhen Development and Reform Commission (Discipline Construction Program), the Shenzhen Peacock Plan (No. KQTD20150717103157174) and the Shenzhen Nobel Prize Scientists Laboratory Project (No. C17783101)the Shenzhen Science and Technology Innovation Committee Basic Research Discipline Layout Project and Peacock Technology Innovation JCYJ20170817110515599the Shenzhen Peacock Plan KQTD20150717103157174the Shenzhen Science and Technology Innovation Committee Basic Research Discipline Layout Project and Peacock Technology Innovation KQJSCX2017072815423320

Figures(3)

The synthesis of the AC ring moiety of daphnilactone B has been achieved through an efficient Diels-Alder reaction and Au-catalyzed Conia-ene reaction in seven steps with 30% overall yield.Our strategies paved the way to the total synthesis of various daphnilactone B-type Daphniphyllum alkaloids.
- daphniphyllum alkaloid,
- daphnilactone B,
- Diels-Alder reaction,
- Conia-ene reaction,
- total synthesis
1. [1]
2. [2]
  Sasaki, K.; Hirata, Y.Tetrahedron Lett.1972, 13, 1891. doi: 10.1016/S0040-4039(01)84744-4
3. [3]
  Yamamura, S.; Terada, Y.Chem.Lett.1976, 5, 1381. doi: 10.1246/cl.1976.1381
4. [4]
  Kong, N.-C.; He, H.-P.; Wang, Y.-H.; Mu, S.-Z.; Di, Y.-T.; Hao, X.-J.J.Nat.Prod.2007, 70, 1348. doi: 10.1021/np0700220
5. [5]
  Zhan, Z.-J.; Zhang, C.-R.; Yue, J.-M.Tetrahedron 2005, 61, 11038. doi: 10.1016/j.tet.2005.03.146
6. [6]
  For synthetic studies published after Ref.[1c], see:
  (a) Li, J.L.; Shi, H.W.; Wang, Q.; Chai, Y.H.; Yang, J.Org.Lett.2017, 19, 1497.
  (b) Boissarie, P.; Bélanger, G.Org.Lett.2017, 19, 3739.
  (c) Liu, Y.M.; Li, F.; Wang, Q.; Yang, J.Tetrahedron 2017, 73, 6381.
  (d) Shao, H.; Bao, W.; Jing, Z.-R.; Wang, Y.-P.; Zhang, F.-M.; Wang, S.-H.; Tu, Y.-Q.Org.Lett.2017, 19, 4648.
  (e) Lopez, A.M.; Ibrahim, A.A.; Rosenhauer, G.J.; Sirinimal, H.S.; Stockdill, J.L.Org.Lett.2018, 20, 2216.
  (f) Sasano, Y.; Koyama, J.; Yoshikawa, K.; Kanoh, N.; Kwon, E.; Iwabuchi, Y.Org.Lett.2018, 20, 3053.
  (g) Yamada, R.; Fukuyama, T.; Yokoshima, S.Org.Lett.2018, 20, 4504.
  (h) Li, Y.; Dong, Q.; Xie, Q.; Tang, P.; Zhang, M.; Qin, Y.Org.Lett.2018, 20, 5053.
  (i) Qiu, Y.; Zhong, J.; Du, S.; Gao, S.Chem.Commun.2018, 54, 5554.
  (j) Kitabayashi, Y.; Fukuyama, T.; Yokoshima, S.Org.Biomol.Chem.2018, 16, 3556.
  (k) Mo, X.-F.; Li, Y.-F.; Sun, M.-H.; Dong, Q.-Y.; Xie, Q.-X.; Tang, P.; Xue, F.; Qin, Y.Tetrahedron Lett.2018, 59, 1999.
  (l) Cox, J.B.; Wood, J.L.Tetrahedron 2018, 74, 4539.
7. [7]
  (a) Heathcock, C.H.; Davidsen, S.K; Mills, S.; Sanner, M.A.J.Am.Chem.Soc.1986, 108, 5650.
  (b) Ruggeri, R.B.; Hansen, M.M.; Heathcock, C.H.J.Am.Chem.Soc.1988, 110, 8734.
  (c) Ruggeri, R.B.; McClure, K.F.; Heathcock, C.H.J.Am.Chem.Soc.1989, 111, 1530.
  (d) Ruggeri, R.B.; Heathcock, C.H.J.Org.Chem.1990, 55, 3714.
  (e) Stafford, J.A.; Heathcock, C.H.J.Org.Chem.1990, 55, 5433.
  (f) Piettre, S.; Heathcock, C.H.Science 1990, 248, 1532.
  (g) Heathcock, C.H.; Stafford, J.A.; Clark, D.L.J.Org.Chem.1992, 57, 2575.
  (h) Heathcock, C.H.Angew.Chem., Int.Ed.Engl.1992, 31, 665.
  (i) Heathcock, C.H.; Joe, D.J.Org.Chem.1995, 60, 1131.
  (j) Heathcock, C.H.; Kath, J.C.; Ruggeri, R.B.J.Org.Chem.1995, 60, 1120.
  (k) Heathcock, C.H.Proc.Natl.Acad.Sci.U.S.A. 1996, 93, 14323.
  (l) Wallace, G.A.; Heathcock, C.H.J.Org.Chem.2001, 66, 450.
8. [8]
  Weiss, M.E.; Carreira, E.M.Angew.Chem., Int.Ed.2011, 50, 11501. doi: 10.1002/anie.v50.48
9. [9]
  (a) Shvartsbart, A.; Smith, A.B.Ⅲ J.Am.Chem.Soc.2014, 136, 870.
  (b) Shvartsbart, A.; Smith, A.B.Ⅲ J.Am.Chem.Soc.2015, 137, 3510.(a) Shvartsbart, A.; Smith, A.B.Ⅲ J.Am.Chem.Soc.2014, 136, 870.
  (b) Shvartsbart, A.; Smith, A.B.Ⅲ J.Am.Chem.Soc.2015, 137, 3510.
10. [10]
  (a) Lu, Z.; Li, Y.; Deng, J.; Li, A.Nat.Chem.2013, 5, 679.
  (b) Xiong, X.; Li, Y.; Lu, Z.; Wan, M.; Deng, J.; Wu, S.; Shao, H.; Li, A.Chem.Commun.2014, 50, 5294.
  (c) Li, J.; Zhang, W.; Zhang, F.; Chen, Y.; Li, A.J.Am.Chem.Soc.2017, 139, 14893.
  (d) Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A.Angew.Chem., Int.Ed.2018, 57, 952.
  (e) Zhang, W.; Ding, M.; Li, J.; Guo, Z.; Lu, M.; Chen, Y.; Liu, L.; Shen, Y.-H.; Li, A.J.Am.Chem.Soc.2018, 140, 4227.
11. [11]
  For the total synthesis of a putative natural Daphniphyllum alkaloid isodaphlongamine H: Chattopadhyay, A.K.; Ly, V.L.; Jakkepally, S.; Berger, G.; Hanessian, S.Angew.Chem., Int.Ed.2016, 55, 2577.
12. [12]
  Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T.Angew.Chem., Int.Ed.2016, 55, 6067. doi: 10.1002/anie.201601958
13. [13]
  Chen, X.; Zhang, H.-J.; Yang, X.; Lv, H.; Shao, X.; Tao, C.; Wang, H.; Cheng, B.; Li, Y.; Guo, J.; Zhang, J.; Zhai, H.Angew.Chem., Int.Ed.2018, 57, 947. doi: 10.1002/anie.201709762
14. [14]
  Shi, H.; Michaelides, I.N.; Darses, B.; Jakubec, P.; Nguyen, Q.N.N.; Paton, R.S.; Dixon, D.J.J.Am.Chem.Soc.2017, 139, 17755. doi: 10.1021/jacs.7b10956
15. [15]
  Denmark, S.E.; Baiazitov, R.Y.J.Org.Chem.2006, 71, 593. doi: 10.1021/jo052001l
16. [16]
  (a) Denmark, S.E.; Baiazitov, R.Y.; Nguyen, S.T.Tetrahedron 2009, 65, 6535.
  (b) Denmark, S.E.; Nguyen, S.T.; Baiazitov, R.Y.Heterocycles 2008, 76, 143.
17. [17]
  Coldham, I.; Burrell, A.J.M.; Guerrand, H.D.S.; Oram, N.Org.Lett.2011, 13, 1267. doi: 10.1021/ol102961x
18. [18]
  (a) Staben, S.T.; Kennedy-Smith, J.J.; Huang, D.; Corkey, B.K.; Lalonde, R.L.; Toste, F.D.Angew.Chem., Int.Ed.2006, 45, 5991.
  (b) Huwyler, N.; Carreira, E.M.Angew.Chem., Int.Ed.2012, 51, 13066. For a Conia-ene reaction catalyzed by Rh, see: :
  (c) Long, R.; Huang, J.; Shao, W.; Liu, S.; Lan, Y.; Gong, J.; Yang, Z.Nat.Commun.2014, 5, 5707.
19. [19]
  Kozmin, S.A.; Rawal, V.H.J.Org.Chem.1997, 62, 5252. doi: 10.1021/jo970438q
20. [20]
  Terrasson, V.; van der Lee, A.; Marcia de Figueiredo, R.; Campagne, J.M.Chem.-Eur.J.2010, 16, 7875. doi: 10.1002/chem.201000334
21. [21]
  Zhang, P.-P.; Yan, Z.M.; Li, Y.-H.; Gong, J.-X.; Yang, Z.J.Am.Chem.Soc.2017, 139, 13989. doi: 10.1021/jacs.7b07388
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