Studies toward Total Synthesis of (±)-Caldaphnidine C via One-Pot Sequential Intramolecular Vilsmeier-Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition

Journal of Organic Chemistry

Volumn 81, Issue 19, 2016, Pages 9247-9268

  Boudreault, Jonathan ^a   Lévesque, François ^a   Bélanger, Guillaume ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; SYNTHESIS (CHEMICAL);

1 ,3-DIPOLARCYCLOADDITION; AZOMETHINE YLIDES; DERIVATIZATIONS; PERFECT CONTROLS; QUATERNARY CENTERS; STEREOGENIC CENTERS; SYNTHETIC STRATEGIES; TOTAL SYNTHESIS;

CYCLIZATION;

AZOMETHINE YLIDE; CALDAPHNIDINE C; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYCLOADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; VILSMEIER HAACK REACTION;

EID: 84990862103     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b01835     Document Type: Article

References (70)

1. Kang, B.; Jakubec, P.; Dixon, D. J. Nat. Prod. Rep. 2014, 31, 550-562 and references cited therein 10.1039/c3np70115h
2. Yang, T.-Q.; Di, Y.-T.; He, H.-P.; Zhang, Q.; Zhang, Y.; Hao, X.-J. Helv. Chim. Acta 2011, 94, 397-403 10.1002/hlca.201000170
3. Dong, M.; Zhang, M.-L.; Shi, Q.-W.; Gu, Y.-C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646-682 10.2174/138527209787847345
4. Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem., Int. Ed. 2016, 55, 2577-2581 10.1002/anie.201510861
5. Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2016, 55, 6067-6070 10.1002/anie.201601958
6. Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2014, 136, 870-873 10.1021/ja411539w
7. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120-1130 10.1021/jo00110a013
8. Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575-2585 10.1021/jo00035a011
9. Stafford, J. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5433-5434 10.1021/jo00307a006
10. Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734-8736 10.1021/ja00234a046
11. Heathcock, C. H.; Davidsen, S. K.; Mills, S.; Sanner, M. A. J. Am. Chem. Soc. 1986, 108, 5650-5651 10.1021/ja00278a061
12. Chattopadhyay, A. K.; Berger, G.; Hanessian, S. J. Org. Chem. 2016, 81, 5074-5086 and references cited therein 10.1021/acs.joc.6b00638
13. Diaba, F.; Martínez-Laporta, A.; Coussanes, G.; Fernández, I.; Bonjoch, J. Tetrahedron 2015, 71, 3642-3651 and references cited therein 10.1016/j.tet.2014.11.044
14. Wang, W.; Li, G.-P.; Wang, S.-F.; Shi, Z.-F.; Cao, X.-P. Chem.-Asian J. 2015, 10, 377-382 and references cited therein 10.1002/asia.201403152
15. Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2015, 137, 3510-3519 10.1021/ja503899t
16. Williams, D. R.; Mondal, P. K.; Bawel, S. A.; Nag, P. P. Org. Lett. 2014, 16, 1956-1959 10.1021/ol5005092
17. Yang, M.; Wang, L.; Wang, S.-H.; Zhang, S.-Y.; Tu, Y.-Q.; Zhang, F.-M.; He, Z.-H. Org. Lett. 2012, 14, 5114-5117 10.1021/ol302386g
18. Darses, B.; Michaelides, I. N.; Sladojevich, F.; Ward, J. W.; Rzepa, P. R.; Dixon, D. J. Org. Lett. 2012, 14, 1684-1687 and references cited therein 10.1021/ol3002267
19. Denmark, S. E.; Baiazitov, R. Y. J. Org. Chem. 2006, 71, 593-605 10.1021/jo052001l
20. Denmark, S. E.; Baiazitov, R. Y.; Nguyen, S. T. Tetrahedron 2009, 65, 6535-6548 10.1016/j.tet.2009.05.060
21. Denmark, S. E.; Nguyen, S. T.; Baiazitov, R. Y. Heterocycles 2008, 76, 143-154 10.3987/COM-08-S(N)15
22. Hayakawa, I.; Niida, K.; Kigoshi, H. Chem. Commun. 2015, 51, 11568-11571 10.1039/C5CC03479E
23. Coldham, I.; Burrell, A. J. M.; Guerrand, H. D. S.; Oram, N. Org. Lett. 2011, 13, 1267-1269 10.1021/ol102961x
24. Coldham, I.; Watson, L.; Adams, H.; Martin, N. G. J. Org. Chem. 2011, 76, 2360-2366 10.1021/jo2000868
25. Hanessian, S.; Dorich, S.; Menz, H. Org. Lett. 2013, 15, 4134-4137 10.1021/ol4018112
26. Bélanger, G.; Boudreault, J.; Lévesque, F. Org. Lett. 2011, 13, 6204-6207 10.1021/ol202629d
27. Lévesque, F.; Bélanger, G. Org. Lett. 2008, 10, 4939-4942 10.1021/ol802010n
28. Bélanger, G.; Darsigny, V.; Doré, M.; Lévesque, F. Org. Lett. 2010, 12, 1396-1399 10.1021/ol902767b
29. Kallury, K. R.; Krull, U. J.; Thompson, M. J. Org. Chem. 1988, 53, 1320-1322 10.1021/jo00241a040
30. Minami, I.; Nisar, M.; Yuhara, M.; Shimizu, I.; Tsuji, J. Synthesis 1987, 1987, 992-998 10.1055/s-1987-28145
31. Yu, J.-Q.; Wu, H.-C.; Corey, E. J. Org. Lett. 2005, 7, 1415-1417 10.1021/ol050284y
32. Lippert, A. R.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 14738-14739 10.1021/ja063900+
33. Okabayashi, T.; Iida, A.; Takai, K.; Nawate, Y.; Misaki, T.; Tanabe, Y. J. Org. Chem. 2007, 72, 8142-8145 10.1021/jo701456t
34. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817-826 10.1002/anie.197708171
35. Hergueta, A. R.; López, C.; Fernández, F.; Caamano, O.; Blanco, J. M. Tetrahedron: Asymmetry 2003, 14, 3773-3778 10.1016/j.tetasy.2003.09.033
36. Stork, G.; Wagle, S. S.; Mukharji, P. C. J. Am. Chem. Soc. 1953, 75, 3197-3204 10.1021/ja01109a046
37. Peters, R. J.; Ravn, M. M.; Coates, R. M.; Croteau, R. B. J. Am. Chem. Soc. 2001, 123, 8974-8978 10.1021/ja010670k
38. Pasqua, A. E.; Matheson, M.; Sewell, A. L.; Marquez, R. Org. Process Res. Dev. 2011, 15, 467-470 10.1021/op200011x
39. Katritzky, A. R.; Chang, H.-X.; Yang, B. Synthesis 1995, 1995, 503-505 10.1055/s-1995-3959
40. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
41. Pu, X.; Ma, D. J. Org. Chem. 2006, 71, 6562-6572 10.1021/jo061070c
42. Pelphrey, P. M.; Popov, V. M.; Joska, T. M.; Beierlein, J. M.; Bolstad, E. S. D.; Fillingham, Y. A.; Wright, D. L.; Anderson, A. C. J. Med. Chem. 2007, 50, 940-950 10.1021/jm061027h
43. Kitajima, M.; Takayama, H.; Sakai, S.-I. J. Chem. Soc., Perkin Trans. 1 1991, 1773-1779 10.1039/p19910001773
44. Spino, C.; Joly, M.-A.; Godbout, C.; Arbour, M. J. Org. Chem. 2005, 70, 6118-6121 10.1021/jo050712d
45. Busch-Petersen, J.; Hill, W. A.; Fan, P.; Khanolkar, A.; Xie, X.-Q.; Tius, M. A.; Makriyannis, A. J. Med. Chem. 1996, 39, 3790-3796 10.1021/jm950934b
46. 4 more important than that of silicon. See: Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961 10.1021/ja00013a035
47. A remarkable example of this is reported by Pearson. See: Pearson, W. H.; Dietz, A.; Stoy, P. Org. Lett. 2004, 6, 1005-1008 10.1021/ol0499304
48. Hajra, S.; Mandal, A.; Hazra, S. Tetrahedron Lett. 2013, 54, 2171-2173 10.1016/j.tetlet.2013.02.044
49. Hajra, S.; Giri, A. K.; Hazra, S. J. Org. Chem. 2009, 74, 7978-7981 10.1021/jo900810a
50. Yinglin, H.; Hongwen, H. Synthesis 1990, 1990, 122-124 10.1055/s-1990-26805
51. Kantlehner, W. Eur. J. Org. Chem. 2003, 2003, 2530-2546 10.1002/ejoc.200200653
52. Kulkarni, M. G.; Davawala, S. I.; Doke, A. K.; Pendharkar, D. S. Synthesis 2004, 2919-2926 10.1055/s-2004-831208
53. Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654 10.1021/ol006182j
54. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408 10.1016/S0040-4039(00)85909-2
55. Nicolaou, K. C.; Yue, E. W.; la Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; de Riccardis, F. Chem.-Eur. J. 1995, 1, 467-494 10.1002/chem.19950010712
56. Vedejs, E.; Grissom, J. W. J. Org. Chem. 1988, 53, 1876-1882 10.1021/jo00244a008
57. Siebum, A. H. G.; Woo, W. S.; Lugtenburg, J. Eur. J. Org. Chem. 2003, 2003, 4664-4678 10.1002/ejoc.200300410
58. Guindon, Y.; Yoakim, C.; Morton, H. E. Tetrahedron Lett. 1983, 24, 2969-2972 10.1016/S0040-4039(00)88071-5
59. Roberts, S. W.; Rainier, J. D. Org. Lett. 2007, 9, 2227-2230 10.1021/ol0707970
60. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956 10.1021/ol990909q
61. Friedrich, J.; Dolg, M.; Gansäuer, A.; Geich-Gimbel, D.; Lauterbach, T. J. Am. Chem. Soc. 2005, 127, 7071-7077 10.1021/ja050268w
62. Campbell, E. L.; Zuhl, A. M.; Liu, C. M.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3009-3012 10.1021/ja908819q
63. Cocquet, G.; Rool, P.; Ferroud, C. J. Chem. Soc., Perkin Trans. 1 2000, 2277-2281 10.1039/b001114m
64. Amat, M.; Gómez-Esqué, A.; Escolano, C.; Santos, M. M. M.; Molins, E.; Bosch, J. J. Org. Chem. 2009, 74, 1205-1211 10.1021/jo802387c
65. Cimarelli, C.; Palmieri, G. J. Org. Chem. 1996, 61, 5557-5563 10.1021/jo960107y
66. Maury, C.; Wang, Q.; Gharbaoui, T.; Chiadmi, M.; Tomas, A.; Royer, J.; Husson, H.-P. Tetrahedron 1997, 53, 3627-3636 10.1016/S0040-4020(97)00086-0
67. Agami, C.; Couty, F.; Evano, G.; Darro, F.; Kiss, R. Eur. J. Org. Chem. 2003, 2003, 2062-2070 10.1002/ejoc.200300057
68. Nielsen, S. F.; Kharazmi, A.; Christensen, S. B. Bioorg. Med. Chem. 1998, 6, 937-945 10.1016/S0968-0896(98)00051-0
69. Santos, P. F.; Srinivasan, N.; Almeida, P. S.; Lobo, A. M.; Prabhakar, S. Tetrahedron 2005, 61, 9147-9156 10.1016/j.tet.2005.07.030
70. The excess of phenyldimethylsilylcuprate reacts with the excess of ethyl chloroformate to give ethyl phenyldimethylsilanecarboxylate as a side product. The latter could be separated from compound 30 with a careful flash chromatography, but could also be carried on to the next step. Saponification conditions give the corresponding phenyldimethylsilanol that could pumped off (b.p. 101-101.4 °C, 14 mm Hg) at 50 °C under high vacuum (ca. 0.01 mm Hg) over 6 h. See: Hyde, J. F.; Johannson, O. K.; Daudt, W. H.; Fleming, R. F.; Laudenslager, H. B.; Roche, M. P. J. Am. Chem. Soc. 1953, 75, 5615-5618 10.1021/ja01118a042