Citation: Zhang Yuping, Tian Xuechao, Zhang Yan, Hong Ran, Huang Shahua. Methods and Strategies for the Synthesis of Peduncularine[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 47-58. doi: 10.6023/cjoc201810008 shu

Methods and Strategies for the Synthesis of Peduncularine

Zhang Yuping ^a ,
Tian Xuechao ^a ,
Zhang Yan ^b ,
Hong Ran ^b,, ,
Huang Shahua ^a,b,,

a.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418
b.
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Hong Ran, rhong@sioc.ac.cn Huang Shahua, shahua@sit.edu.cn
Received Date: 9 October 2018
Revised Date: 22 November 2018
Available Online: 5 January 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21402121) and the Collaborative Innovation Program of Shanghai Institute of Technology (No. XTCX2015-16)the Collaborative Innovation Program of Shanghai Institute of Technology XTCX2015-16Project supported by the National Natural Science Foundation of China 21402121

Figures(16)

(-)-Peduncularine is the principal alkaloid isolated from Tasmanian shrub Aristotelia peduncularis. Due to its unusual 6-azabicyclo[3.2.1]octane core, the indole alkaloid was received numerous attention from the synthetic community and several innovative synthetic strategies have been developed. In this minireview, the synthetic efforts of peduncularine are summarized as inspiration for future development of medicinally interesting derivatives.
- 6-azabicyclo[3.2.1]octane,
- cyclization,
- indole alkaloids,
- peduncularine,
- total synthesis
1. [1]
  (a) Butler, M. S. J. Nat. Prod. 2004, 67, 2141.
  (b) Li, J. W.-H.; Vederas, J. C. Science 2009, 325, 161.
  (c) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2016, 79, 629.
  (d) DeCorte, B. L. J. Med. Chem. 2016, 59, 9295.
2. [2]
  Lawson, A. D. G.; MacCoss, M.; Heer, J. P. J. Med. Chem. 2018, 61, 4283. doi: 10.1021/acs.jmedchem.7b01120
3. [3]
  Over, B.; Wetzel, S.; Grütter, C.; Nakai, Y.; Renner, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2013, 5, 21. doi: 10.1038/nchem.1506
4. [4]
  Bick, I. R. C.; Bremner, J. B.; Preston, N. W.; Calder, I. C. J. Chem. Soc., Chem. Commun. 1971, 1155.
5. [5]
  Ros, H.-P.; Kyburz, R.; Preston, N. W.; Gallagher, R. T.; Bick, I. R. C.; Hesse, M. Helν. Chim. Acta 1979, 62, 481. doi: 10.1002/(ISSN)1522-2675
6. [6]
  Bick, I. R. C.; Hai, M. A.; Preston, N. W. Tetrahedron 1985, 41, 3127. doi: 10.1016/S0040-4020(01)96665-7
7. [7]
  Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588. doi: 10.1021/ja00189a036
8. [8]
  Dragar, C.; Bick, I. R. C. Phytochemistry 1992, 31, 3601. doi: 10.1016/0031-9422(92)83734-G
9. [9]
  (a) Singh, S. Chem. Rev. 2000, 100, 925.
  (b) Pollini, G. P.; Benetti, S.; De Risi, C.; Zanirato, V. Chem. Rev. 2006, 106, 2434.
10. [10]
  (a) Carroll, F. I.; Abraham, P.; Parham, K.; Griffith, R. C.; Ahmad, A.; Richard, M. M.; Padilla, F. N.; Witkin, J. M.; Chiang, P. K. J. Med. Chem. 1987, 30, 805.
  (b) Carroll, F. I.; Abraham, P.; Mascarella, S. W.; Singh, P.; Moreland, C. G.; Sankar, S. S.; Kwon, Y. W.; Triggle, D. J. J. Med. Chem. 1991, 34, 1436.
11. [11]
  Quirante, J.; Vila, X.; Bonjoch, J.; Kozikowski, A. P.; Johnson, K. M. Bioorg. Med. Chem. 2004, 12, 1383.
12. [12]
  Holmes, A. B.; Kee, A.; Ladduwahetty, T.; Smith, D. F. J. Chem. Soc., Chem. Commun. 1990, 1412.
13. [13]
  Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653. doi: 10.1021/ja00349a051
14. [14]
  (a) Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1983, 24, 1407.
  (b) Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. J. Org. Chem. 1984, 49, 1149.
15. [15]
  Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.-O. Org. Synth. 1984, 62, 158. doi: 10.15227/orgsyn.062.0158
16. [16]
  Robinson, B. Chem. Rev. 1969, 69, 227. doi: 10.1021/cr60258a004
17. [17]
  Rigby, J. H.; Meyer, J. H. Synlett 1999, 860.
18. [18]
  Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M. Sugathapala, P. M. Tetrahedron 1993, 49, 5495. doi: 10.1016/S0040-4020(01)87265-3
19. [19]
  McKillop, A.; Hunt, J. D.; Kienzle, F.; Bigham, E.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3635. doi: 10.1021/ja00792a028
20. [20]
  Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333. doi: 10.1016/S0040-4039(00)00194-5
21. [21]
  (a) Hudson, R. F.; Record, K. A. F. J. Chem. Soc., Perkin. 21978, 822.
  (b) Lin, X.; Stien, D.; Weinreb, S. M. Org. Lett. 1999, 1, 637.
22. [22]
  (a) Washburn, D. G.; Heidebrecht, R. W., Jr.; Martin, S. F. Org. Lett. 2003, 5, 3523.
  (b) Martin, S. F. Pure Appl. Chem. 2005, 77, 1207.
23. [23]
  (a) Brown, D. S.; Hansson, T.; Ley, S. V. Synlett 1990, 48.
  (b) Brown, D. S.; Charreu, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311.
24. [24]
  Roberson, C. W.; Woerpel, K. A. Org. Lett. 2000, 2, 621. doi: 10.1021/ol9913744
25. [25]
  Durst, T.; O'Sullivan, M. J. J. Org. Chem. 1970, 35, 2043. doi: 10.1021/jo00831a081
26. [26]
  Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434. doi: 10.1021/jo982375x
27. [27]
  Dubé, D.; Scholte, A. A. Tetrahedron Lett. 1999, 40, 2295. doi: 10.1016/S0040-4039(99)00211-7
28. [28]
  Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517. doi: 10.1021/jo9805652
29. [29]
  Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694. doi: 10.1021/om50005a041
30. [30]
  Roberson, C. W.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 11342. doi: 10.1021/ja012152f
31. [31]
  Shute, R. E.; Rich, D. H. Synthesis 1987, 346.
32. [32]
  (a) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295.
  (b) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
33. [33]
  Roush, W. R.; Gillis, H. R. J. Org. Chem. 1980, 45, 4283. doi: 10.1021/jo01310a006
34. [34]
  Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849. doi: 10.1021/jo960057x
35. [35]
  Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044. doi: 10.1021/jo960921l
36. [36]
  Parikh, J. R.; Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505. doi: 10.1021/ja00997a067
37. [37]
  Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386. doi: 10.1021/jo00213a040
38. [38]
  Hodgson, D. M.; Shelton, R. E.; Moss, T. A.; Dekhane, M. Org. Lett. 2010, 12, 2834.
39. [39]
  Mann, J.; de Almeida Barbosa L.-C. J. Chem. Soc., Perkin Trans. 1 1992, 787.
40. [40]
  Davies, H. M. L.; Cao, G. Tetrahedron Lett. 1998, 39, 5943. doi: 10.1016/S0040-4039(98)01221-0
41. [41]
  Swallen, L. C.; Boord, C. E. J. Am. Chem. Soc. 1930, 52, 651. doi: 10.1021/ja01365a033
42. [42]
  Kitamura, M.; Ihara, R.; Uera, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 2006, 79, 1552. doi: 10.1246/bcsj.79.1552
43. [43]
  (a) Uchiyama, K.; Ono, A.; Hayashi, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1998, 71, 2945.
  (b) Uchiyama, K.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1998, 1261.
44. [44]
  Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339.
45. [45]
  Lenz, G. R.; Woo, ; Hawkins, B. L. J. Org. Chem. 1982, 47, 3049. doi: 10.1021/jo00137a004
46. [46]
  (a) Hudrlik, P. F.; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
  (b) Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
47. [47]
  Ragains, J. R.; Winkler, J. D. Org. Lett. 2006, 8, 4437. doi: 10.1021/ol061577+
48. [48]
  (a) Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 110, 4831.
  (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429.
49. [49]
  Comins, D. L; Dehghani. A. Tetrahedron Lett. 1992, 33, 6299. doi: 10.1016/S0040-4039(00)60957-7
50. [50]
  Jigqjinni, V. B.; Wightman, R. H. Tetrahedron Lett. 1982, 23, 117. doi: 10.1016/S0040-4039(00)97549-X
51. [51]
  (a) Kyburz, R.; Schöpp, E.; Hesse, M.; Bick, I. R. C. Helv. Chim. Acta 1979, 62, 2539.
  (b) Bick, I. R. C.; Hai, M. A.; Preston, N. W. Tetrahedron Lett. 1988, 29, 3355.
  (c) Anderson, B. F.; Robertson, G. B.; Avey, P.; Donovan, W. F.; Bick, I. R. C.; Bremner, J. B.; Finney, A. J.T.; Preston, N. W.; Gallagher, R. T.; Russell, G. B. J. Chem. Soc., Chem. Commun. 1975, 511.
  (d) Bittner, M.; Silva, M.; Gopalakrishna, E. M.; Watson, W. H.; Zabel, V.; Matlin, S. A.; Sammes, P. G. J. Chem. Soc., Chem. Commun. 1978, 79.
52. [52]
  (a) Bick, I. R. C.; Hai, M. A.; Preston, N. W. Heterocycles 1979, 12, 1563.
  (b) Saxton, J. E. Nat. Prod. Rep. 1994, 11, 493.
  (c) An elegant review on the biomimetic synthesis study of aristotelia alkaloids, see: Borschberg, H.-J. In The Alkaloids: Chemistry and Pharmacology, Vol. 48, Ed.: Cordell, G. A., Elsevier, Academic Press, 1996, Chapter 3, pp. 191~248.
53. [53]
  (a) Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752.
  (b) Szychowski, J.; Truchon, J.-F.; Bennani, Y. L. J. Med. Chem. 2014, 57, 9292.
  (c) Stockdale, T. P.; Williams. C. M. Chem. Soc. Rev. 2015, 44, 7737.
54. [54]
  (a) Tamura, O.; Yanagimachi, T.; Kobayashi, T.; Ishibashi, H. Org. Lett. 2001, 3, 2427.
  (b) Zhai, H.-B.; Luo, S.-J.; Ye, C.-F.; Ma, Y.-X. J. Org. Chem. 2003, 68, 8268.
  (c) Yeung, Y. Y.; Hong, S.-W.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310.
  (d) Grainger, R. S.; Welsh, E. J. Angew. Chem., Int. Ed. 2007, 46, 5477.
  (e) Campbell, C. L.; Hassler, C.; Ko, S. S.; Voss, M. E.; Guaciaro, M. A.; Carter, P. H.; Cherney, R. J. J. Org. Chem. 2009, 74, 6368.
55. [55]
  Kanchupalli, V.; Katukojvala, S. Angew. Chem., Int. Ed. 2018, 57, 5433. doi: 10.1002/anie.v57.19
56. [56]
  Zhan, Y.-Z.; Liu, T.; Wang, Z.-W. Chem. Eur. J. 2017, 23, 17862. doi: 10.1002/chem.v23.71
57. [57]
  Mackiewicz, P.; Furstoss, R.; Waegell, B. J. Org. Chem. 1978, 43, 3746. doi: 10.1021/jo00413a026
58. [58]
  Liu, T.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 5871. doi: 10.1021/jacs.5b02065
59. [59]
  Holmes, A. B.; Raithby, P. R.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1983, 1490.
60. [60]
  (a) Callis, D. J.; Thomas, N. F.; Pearson, D. P. J.; Potter, B. V. L. J. Org. Chem. 1996, 61, 4634.
  (b) Kumar, P.; Li, P.-H.; Korboukh, I.; Wang, T. L.; Yennawar, H.; Weinreb, S. M. J. Org. Chem. 2011, 76, 2094.
61. [61]
  (a) Xie, C.; Luo, J.; Zhang, Y.; Huang, S.-H.; Zhu, L.; Hong, R. Org. Lett. 2018, 20, 2386.
  (b) Luo, J.; Xie, C.; Zhang, Y.; Huang, S.-H.; Zhu, L.; Hong, R. Tetrahedron 2018, 74, 5791.
62. [62]
  Quirante, J.; Vila, X.; Escolano, C.; Bonjoch, J. J. Org. Chem. 2002, 67, 2323. doi: 10.1021/jo0163849
63. [63]
  Grainger, R. S.; Betou, M.; Male, L.; Pitak, M. B.; Coles, S. J. Org. Lett. 2012, 14, 2234. doi: 10.1021/ol300605y
64. [64]
  Walker, P. D.; Campbell, C. D.; Suleman, A.; Carr, G.; Anderson, E. A. Angew. Chem., Int. Ed. 2013, 52, 9139. doi: 10.1002/anie.201304186
65. [65]
  Yeh, M.-C. P.; Chang, Y.-M.; Lin, H.-H. Adv. Synth. Catal. 2017, 359, 2196. doi: 10.1002/adsc.v359.13
1. [1]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
2. [2]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
3. [3]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
4. [4]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
5. [5]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
6. [6]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
7. [7]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
8. [8]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
9. [9]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
10. [10]
  Wenxu Liu , Feng Han , Boxuan Wang , Huayi Liu , Xiaobin Gu , Xin Zhang , Yao Liu . Comprehensive Chemical Experiment: Design, Synthesis, and Photoelectronic Properties Study of Fully Non-Fused Ring Electron Acceptors. University Chemistry, 2025, 40(10): 263-275. doi: 10.12461/PKU.DXHX202412021
11. [11]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
12. [12]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
13. [13]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
14. [14]
  Shumin Zhang , Yaqi Wang , Zelin Wang , Libo Wang , Changsheng An , Difa Xu . Ultrafast electron transfer at the ZIS_1−x/UCN S-scheme interface enables efficient H₂O₂ photosynthesis coupled with tetracycline degradation. Acta Physico-Chimica Sinica, 2025, 41(11): 100136-0. doi: 10.1016/j.actphy.2025.100136
15. [15]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
16. [16]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
17. [17]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
18. [18]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
19. [19]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
20. [20]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046

Get Citation

PDF

XML

Metrics

PDF Downloads(42)
Abstract views(2427)
HTML views(402)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142