Citation: Hu Jiadong, Wen Wen. Progress in the Stereoselective Construction of Chiral 4-Substituted Chroman Skeleton[J]. Chemistry, ;2020, 83(9): 799-804. shu

Progress in the Stereoselective Construction of Chiral 4-Substituted Chroman Skeleton

Hu Jiadong ^1,2,, ,
Wen Wen ¹

1.
School of Medicinal and Chemical Engineering, Yangling Vocational & Technical College, Yangling, 712100
2.
College of Chemistry & Pharmacy, Northwest A & F University, Yangling, 712100

Corresponding author: Hu Jiadong, hujiadong@aliyun.com
Received Date: 2 March 2020
Accepted Date: 8 April 2020

Figures(1)

Chiral 4-substituted chroman skeleton is widely found in numerous bioactive natural products and their analogues. The asymmetric construction strategy of this skeleton plays a crucial role in the research of new drugs. In order to provide a reference for the asymmetric synthesis of active natural products containing this skeleton, in this paper the stereoselective forge methods of chiral 4-substituted chroman from addition reaction, hydrogenation reaction, alkylation reaction, ene/propargylation reaction, desymmetrization reaction, carbonyl α-arylation reaction and rearrangement reaction are summarized.
- Chiral 4-substituted chroman skeleton,
- Stereoselectivity,
- Addition reaction,
- Hydrogenation reaction
1. [1]
  Harvey A. IDrugs, 2010, 13(2): 70～72.
2. [2]
  Shaheen F, Ahmad M, Nahar Khan S, et al. Eur. J. Org. Chem., 2006, 2006(10): 2371～2377.
3. [3]
  Salni D, Sargent M V, Skelton B W, et al. Aust. J. Chem., 2002, 55(3): 229～232.
4. [4]
  Cain J C. Nature, 1960, 188: 774～777.
5. [5]
  Kashiwada Y, Yamazaki K, Ikeshiro Y, et al. Tetrahedron, 2001, 57(8): 1559～1563.
6. [6]
  Li Y, Meng Y, Yang Y, et al. Phytochem. Lett., 2014, 10: 46～49.
7. [7]
8. [8]
  Shen H C. Tetrahedron, 2009, 65(20): 3931～3952.
9. [9]
  Zhang X, Zhang S, Wang W. Angew. Chem. Int. Ed., 2010, 49(8): 1481～1484.
10. [10]
  Liu C, Zhang X, Wang R, et al. Org. Lett., 2010, 12(21): 4948～4951.
11. [11]
  Ramachary D B, Sakthidevi R. Org. Biomol. Chem., 2010, 8(19): 4259～4265.
12. [12]
  Du Z, Siau W, Wang J. Tetrahed. Lett., 2011, 52(46): 6137～6141.
13. [13]
  Blay G, Muñoz M C, Pedro J R, et al. Adv. Synth. Catal., 2013, 355(6): 1071～1076.
14. [14]
  Jeong H J, Kim D Y. Org. Lett., 2018, 20(10): 2944～2947.
15. [15]
  Kim H, Yun J. Adv. Synth. Catal., 2010, 352(11/12): 1881～1885.
16. [16]
  Hsiao C, Liao H, Sugiono E, et al. Chem. Eur. J., 2013, 19(30): 9775～9779.
17. [17]
  Terada M, Yamanaka T, Toda Y. Chem. Eur. J., 2013, 19(41): 13658～13662.
18. [18]
  Gao Y, Hou Y, Zhu L, et al. RSC Adv., 2019, 9(50): 29005～29009.
19. [19]
  Gao Y, Du D. Tetrahedron: Asymmetry, 2013, 24(20): 1312～1317.
20. [20]
  Yang Z, He Y, Toste F D. J. Am. Chem. Soc., 2016, 138(31): 9775～9778.
21. [21]
  Fukamizu K, Miyake Y, Nishibayashi Y. J. Am. Chem. Soc., 2008, 130(32): 10498～10499.
22. [22]
  Schafroth M A, Rummelt S M, Sarlah D, et al. Org. Lett., 2017, 19(12): 3235～3238.
23. [23]
  Matsuda T, Shigeno M, Murakami M. J. Am. Chem. Soc., 2007, 129(40): 12086～12087.
24. [24]
  Yang W, Liu Y, Zhang S, et al. Angew. Chem. Int. Ed., 2015, 54(30): 8805～8808.
25. [25]
  Nicolaou K C, Reingruber R, Sarlah D, et al. J. Am. Chem. Soc., 2009, 131(6): 2086～2087.
26. [26]
  Conrad J C, Kong J, Laforteza B N, et al. J. Am. Chem. Soc., 2009, 131(33): 11640～11641.
27. [27]
  Uemura M, Watson I D G, Katsukawa M, et al. J. Am. Chem. Soc., 2009, 131(10): 3464～3465.
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沈阳化工大学材料科学与工程学院沈阳 110142