Total Synthesis of (+)-Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization

Angewandte Chemie - International Edition

Volumn 55, Issue 28, 2016, Pages 8090-8094

  Zhang, Ze Xin ^a   Chen, Si Cong ^a   Jiao, Lei ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

alkaloids; cyclizations; natural products; palladium; total synthesis

Indexed keywords

ALKALOIDS; MONOTERPENES; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

CASCADE CYCLIZATION; CYCLIZATIONS; DEAROMATIZATION; INDOLE ALKALOIDS; MONOTERPENE INDOLE ALKALOIDS; NATURAL PRODUCTS; PALLADIUM-CATALYZED; TOTAL SYNTHESIS;

CYCLIZATION;

EID: 84969951673     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201602771     Document Type: Article

References (69)

1. A.-ur. Rahman, A. Basha, Indole Alkaloids, Harwood, Amsterdam, 1997;
2. G. W. Gribble, Part B: The Indole Alkaloids, Second Supplements to the 2nd ed. of Rodd's Chemistry of Carbon Compounds, Vol. 4, Elsevier, Amsterdam, 1997, pp. 69–164;
3. U. Anthoni, C. Christophersen, P. H. Nielsen in Alkaloids: Chemical and Biological Perspecties, Vol. 14 (Ed.: S. W. Pelletier), Elsevier, New York, 1999, pp. 163–236.
4. V. Saraswathi, V. Mathuram, S. Subramanian, S. Govindasamy, Cancer Biochem. Biophys. 1999, 17, 79–88;
5. A. Ramírez, S. Garcia-Rubío, Curr. Med. Chem. 2003, 10, 1891–1915.
6. For total syntheses of (+)-minfiensine, see:
7. A. B. Dounay, L. E. Overman, A. D. Wrobleski, J. Am. Chem. Soc. 2005, 127, 10186–10187;
8. A. B. Dounay, P. G. Humphreys, L. E. Overman, A. D. Wrobleski, J. Am. Chem. Soc. 2008, 130, 5368–5377;
9. L. Shen, M. Zhang, Y. Wu, Y. Qin, Angew. Chem. Int. Ed. 2008, 47, 3618–3621;
10. Angew. Chem. 2008, 120, 3674–3677;
11. S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606–13607;
12. G. Li, A. Padwa, Org. Lett. 2011, 13, 3767–3769;
13. P. Liu, J. Wang, J. Zhang, F.-G. Qiu, Org. Lett. 2011, 13, 6426–6428;
14. Y. Yu, G. Li, L. Jiang, L. Zu, Angew. Chem. Int. Ed. 2015, 54, 12627–12631;
15. Angew. Chem. 2015, 127, 12818–12822;
16. W. Ji, L. Yao, X. Liao, Org. Lett. 2016, 18, 628–630.
17. For total syntheses of aspidophylline A, see:
18. L. Zu, B. W. Boal, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 8877–8879;
19. M. Teng, W. Zi, D. Ma, Angew. Chem. Int. Ed. 2014, 53, 1814–1817;
20. Angew. Chem. 2014, 126, 1845–1848;
21. W. Ren, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2014, 53, 1818–1821;
22. Angew. Chem. 2014, 126, 1849–1852;
23. J. Moreno, E. Picazo, L. A. Morrill, J. M. Smith, N. K. Garg, J. Am. Chem. Soc. 2016, 138, 1162–1165.
24. For the synthesis of vincorine, see:
25. M. Zhang, X. Huang, L. Shen, Y. Qin, J. Am. Chem. Soc. 2009, 131, 6013–6020;
26. W. Zi, W. Xie, D. Ma, J. Am. Chem. Soc. 2012, 134, 9126–9129;
27. B. D. Horning, D. W. C. MacMillan, J. Am. Chem. Soc. 2013, 135, 6442–6445.
28. M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592–4593.
29. For selected examples, see:
30. M. Bandini, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi, J. Am. Chem. Soc. 2006, 128, 1424–1425;
31. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314–6315;
32. H. Y. Cheung, W.-Y. Yu, F. L. Lam, T. T. L. Au-Yeung, Z. Zhou, T. H. Chan, A. S. C. Chan, Org. Lett. 2007, 9, 4295–4298;
33. Z. Cao, Y. Liu, Z. Liu, X. Feng, M. Zhuang, H. Du, Org. Lett. 2011, 13, 2164–2167;
34. Y. Liu, H. Du, Org. Lett. 2013, 15, 740–743;
35. L. Du, P. Cao, J. Xing, Y. Lou, L. Jiang, L. Li, J. Liao, Angew. Chem. Int. Ed. 2013, 52, 4207–4211;
36. Angew. Chem. 2013, 125, 4301–4305;
37. Q.-L. Xu, L.-X. Dai, S.-L. You, Chem. Sci. 2013, 4, 97–102;
38. L. Pignataro, D. Fiorito, V. Vece, R. Ferraccioli, C. Gennari, Eur. J. Org. Chem. 2015, 6669–6678.
39. For selected recent examples, see:
40. W.-B. Liu, H. He, L.-X. Dai, S.-L. You, Org. Lett. 2008, 10, 1815–1818;
41. L. M. Stanley, J. F. Hartwig, Angew. Chem. Int. Ed. 2009, 48, 7841–7844;
42. Angew. Chem. 2009, 121, 7981–7984;
43. Q.-F. Wu, H. He, W.-B. Liu, S.-L. You, J. Am. Chem. Soc. 2010, 132, 11418–11419;
44. Q.-F. Wu, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 1680–1683;
45. Angew. Chem. 2012, 124, 1712–1715;
46. X. Zhang, L. Han, S.-L. You, Chem. Sci. 2014, 5, 1059–1063;
47. X. Zhang, W.-B. Liu, H.-F. Tu, S.-L. You, Chem. Sci. 2015, 6, 4525–4529;
48. C.-X. Zhuo, Y. Zhou, Q. Cheng, L. Huang, S.-L. You, Angew. Chem. Int. Ed. 2015, 54, 14146–14149;
49. Angew. Chem. 2015, 127, 14352–14355.
50. C.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 12662–12686;
51. Angew. Chem. 2012, 124, 12834–12858;
52. C.-X. Zhuo, C. Zheng, S.-L. You, Acc. Chem. Res. 2014, 47, 2558–2573;
53. S. P. Roche, J.-J. Y. Tendoung, B. Tréguier, Tetrahedron 2015, 71, 3549–3591.
54. During the preparation of this manuscript, a report describing total synthesis of aspidophylline utilizing an iridium-catalyzed allylic alkylation of indole was published. See: S.-Z. Jiang, X.-Y. Zeng, X. Liang, T. Lei, K. Wei, Y.-R. Yang, Angew. Chem. Int. Ed. 2016, 55, 4044–4048;
55. Angew. Chem. 2016, 128, 4112–4116.
56. The compound 3 was prepared in one step from commercially available 2-methyltryptamine following a literature procedure. See: D. Crich, A. Banerjee, J. Org. Chem. 2006, 71, 7106–7109.
57. S. Kumar, V. Kumar, S. S. Chimni, Tetrahedron Lett. 2002, 43, 8029–8031.
58. M. J. Burk, J. G. Allen, J. Org. Chem. 1997, 62, 7054–7057.
59. B. M. Trost, D. L. Van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327–9343.
60. B. M. Trost, R. C. Bunt, Angew. Chem. Int. Ed. Engl. 1996, 35, 99–102;
61. Angew. Chem. 1996, 108, 70–73.
62. D. Yang, G. C. Micalizio, J. Am. Chem. Soc. 2012, 134, 15237–15240.
63. S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843–2859.
64. A. Yasuda, S. Tanaka, K. Oshima, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1974, 96, 6513–6514;
65. Y. Liang, X. Jiang, X.-F. Fu, S. Ye, T. Wang, J. Yuan, Y. Wang, Z.-X. Yu, Chem. Asian J. 2012, 7, 593–604.
66. H. M. M. Bastiaans, J. L. van der Baan, H. C. J. Ottenheijm, J. Org. Chem. 1997, 62, 3880–3889.
67. M. J. Wanner, R. N. A. Boots, B. Eradus, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, Org. Lett. 2009, 11, 2579–2581.
68. A. Y. Hong, C. D. Vanderwal, J. Am. Chem. Soc. 2015, 137, 7306–7309.
69. B. M. Trost, Acc. Chem. Res. 1980, 13, 385–393.