Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5] decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3358-3373

  Vu, Van Ha ^a   Louafi, Fadila ^b   Girard, Nicolas ^c   Marion, Ronan ^a   Roisnel, Thierry ^a   Dorcet, Vincent ^a   Hurvois, Jean Pierre ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b Universite Mentouri Constantine   (Algeria)

^c Institut du Médicament de Strasbourg   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; CYANIDES; ELECTROCHEMICAL OXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ASYMMETRIC SYNTHESIS; CHIRAL SOLVATING AGENTS; DIETHYL ETHERS; PHENYLETHYLAMINES; PIPERIDINE ALKALOIDS; PROTECTING GROUP; STEREO-SELECTIVE; TOTAL SYNTHESIS;

METABOLITES;

8 (1 PHENYL ETHYL) 1,4 DIOXA 8 AZA SPIRO[4.5]DECANE 7 CARBONITRILE; ALKALOID DERIVATIVE; CYANIDE; ETHER; MYRTINE; PETROLEUM ETHER; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ENANTIOMER; EPIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS; TRANSAMINATION; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; CATALYSIS; ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRILES; QUINOLIZINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84899020341     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500104c     Document Type: Article

References (123)

1. Toyooka, N. In Asymmetric Synthesis of Nitrogen Heterocycles; Royer, J., Ed.; Wiley-VCH: Weinheim, 2009.
2. Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley: New York, 1985; Vol. 3, p 1.
3. Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley: New York, 1996; Vol. 10, p 155.
4. Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211
5. Buffat, M. G. P. Tetrahedron 2004, 60, 1701
6. Laschat, S.; Dickner, T. Synthesis 2000, 1781
7. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633
8. Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825
9. Vu, V. H.; Jouanno, L. A.; Cheignon, A.; Roisnel, T.; Dorcet, V.; Sinbandhit, S.; Hurvois, J. P. Eur. J. Org. Chem. 2013, 5464
10. Slosse, P.; Hootelé, C. Tetrahedron Lett. 1978, 397
11. Slosse, P.; Hootelé, C. Tetrahedron 1981, 24, 4287
12. Michael, J. P. Nat. Prod. Rep. 2004, 21, 625
13. Edwards, M. W.; Daly, J. W. J. Nat. Prod. 1988, 51, 1188
14. Ying, Y.; Kim, H.; Hong, J. Org. Lett. 2011, 13, 796
15. Fustero, S.; Moscardó, J.; Sánchez-Roselló, M.; Flores, S.; Guerola, M. Tetrahedron 2011, 67, 7412
16. Pizzuti, M. G.; Minnard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2008, 6, 3464
17. Kumar, R. S. C.; Reddy, G. V.; Shankaraiah, G.; Babu, K. S.; Rao, J. M. Tetrahedron Lett. 2010, 51, 1114
18. Gnamm, C.; Krauter, C. M.; Brödner, K.; Helmchen, G. Chem. - Eur. J. 2009, 15, 2050
19. Gnamm, C.; Krauter, C. M.; Brödner, K.; Helmchen, G. Chem. - Eur. J. 2009, 15, 10514
20. Comins, D. L.; LaMunyon, D. H. J. Org. Chem. 1992, 57, 5807
21. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823
22. Davis, F. A.; Xu, H.; Zhang, J. J. Org. Chem. 2007, 72, 2046
23. Damodar, K.; Das, B. Synthesis 2012, 44, 83
24. Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 20, 3169
25. Abrunhosa-Thomas, I.; Plas, A.; Vogrig, A.; Kandepedu, N.; Chalard, P.; Troin, Y. J. Org. Chem. 2013, 78, 2511
26. Ciblat, S.; Calinaud, P.; Canet, J.-L.; Troin, Y. J. Chem. Soc. Perkin Trans. 1 2000, 353
27. Murali, R. V. N. S.; Chandrasekhar, S. Tetrahedron Lett. 2012, 53, 3467
28. Gouault, N.; Le Roch, M.; de Campos Pinto, G.; David, M. Org. Biomol. Chem. 2012, 10, 5541
29. Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503
30. For the stereoselective synthesis of alkaloid 241D, see: Saha, N.; Chattopadhyay, S. K. J. Org. Chem. 2012, 77, 11056
31. Louafi, F.; Moreau, J.; Shahane, S.; Golhen, S.; Roisnel, T.; Sinbandhit, S.; Hurvois, J. P. J. Org. Chem. 2011, 76, 9720
32. Louafi, F.; Hurvois, J.-P.; Chibani, A.; Roisnel, T. J. Org. Chem. 2010, 75, 5721
33. Libendi, S. S.; Demizu, Y.; Onomura, O. Org. Biomol. Chem. 2009, 7, 351
34. Tajima, T.; Nakajima, A. J. Am. Chem. Soc. 2008, 130, 10496
35. Liu, W.; Ma, Y.; Yin, Y.; Zhao, Y. Bull. Chem. Soc. Jpn. 2006, 79, 577
36. Girard, N.; Hurvois, J.-P.; Moinet, C.; Toupet, L. Eur. J. Org. Chem. 2005, 2269
37. Malassene, R.; Vanquelef, E.; Toupet, L.; Hurvois, J.-P.; Moinet, C. Org. Biomol. Chem. 2003, 1, 547
38. Renaud, T.; Hurvois, J.-P.; Uriac, P. Eur. J. Org. Chem. 2001, 987
39. Le Gall, E.; Hurvois, J.-P.; Sinbandhit, S. Eur. J. Org. Chem. 1999, 2645
40. Yoshida, J.-I.; Itoh, M.; Morita, Y.; Isoe, S. J. Chem. Soc., Chem. Commun. 1994, 549
41. Chiba, T.; Takata, Y. J. Org. Chem. 1977, 42, 2973
42. Andreades, S.; Zahnow, E. W. J. Am. Chem. Soc. 1969, 91, 4181
43. Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc. 2011, 133, 1260
44. Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc. 2011, 133, 1260
45. Shu, X.-Z.; Xia, X.-F.; Yang, Y.-F.; Ji, K.-G.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2009, 74, 7464
46. Hametner, C.; Hemetsberger, M.; Treu, M.; Mereiter, K.; Jordis, U.; Frölich, J. Eur. J. Org. Chem. 2005, 404
47. Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Mismash, B.; Woodward, J. K.; Simonsen, A. J. Tetrahedron Lett. 1995, 36, 7975
48. Sundberg, R. J.; Théret, M.-H.; Wright, L. Org. Prep. Proced. Int. 1994, 26, 386
49. Sundberg, R. J.; Hunt, P. J.; Desos, P.; Gadamasetti, K. G. J. Org. Chem. 1991, 56, 1689
50. Chen, C.-K.; Hortmann, A. G.; Marzabadi, M.-R. J. Am. Chem. Soc. 1988, 110, 4829
51. Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Ochiai, M.; Inegana, M.; Nagao, Y. Tetrahedron Lett. 1988, 29, 6913
52. North, M. Angew. Chem., Int. Ed. 2004, 43, 4126
53. Wagner, A.; Han, W.; Mayer, P.; Ofial, A. R. Adv. Synth. Catal. 2013, 355, 3058
54. Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092
55. Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317
56. Alagiri, K.; Prabhu, R. Org. Biomol. Chem. 2012, 10, 835
57. Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y.; Zhu, C. Chem. Commun. 2011, 47, 2354
58. Singhal, S.; Jain, S. L.; Sain, B. Chem. Commun. 2009, 2371
59. Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005
60. Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173
61. Rueping, M.; Zoller, J.; Fabry, D. C.; Poscharny, K.; Koenigs, R. M.; Weirich, T. E.; Mayer, J. Chem. - Eur. J. 2012, 18, 3478
62. Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94
63. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 12709
64. Kamijo, S.; Hoshikawa, T.; Inoue, M. Org. Lett. 2011, 13, 5928
65. Gomez, J.-M.; Gil, L.; Ferroud, C.; Gateau-Olesker, A.; Martin, M.-T.; Marazano, C. J. Org. Chem. 2001, 66, 4898
66. Cocquet, G.; Rool, P.; Ferroud, C. J. Chem. Soc., Perkin Trans. 1 2000, 2277
67. Ferroud, C.; Cocquet, G.; Guy, A. Tetrahedron Lett. 1999, 40, 5005
68. Santamaria, J.; Kaddachi, M. T.; Ferroud, C. Tetrahedron Lett. 1992, 33, 781
69. Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359
70. Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383
71. Husson, H.-P. J. Nat. Prod. 1985, 6, 894
72. Ma, J.; Chen, W.; Seidel, D. J. Am. Chem. Soc. 2012, 134, 15305
73. Agami, C.; Couty, F.; Evano, G.; Darro, F.; Kiss, R. Eur. J. Org. Chem. 2003, 2062
74. Heathcock, C. H.; Norman, M. H.; Dickman, D. A. J. Org. Chem. 1990, 55, 798
75. Amato, J. S.; Chung, J. Y. L.; Cvetovich, R. L.; Reamer, R. A.; Zhao, D.; Zhou, G.; Gong, X. Org. Prep. Res. Dev. 2004, 8, 939
76. Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701
77. Mistryukov, E. A.; Aronova, N. I.; Kucherov, V. F. Izv. Akad. Nauk SSSR, Ser. Khim. 1961, 932
78. Pawøowska, J.; Krawczyk, K. K.; Wojtasiewicz, K.; Maurin, J. K.; Czarnocki, Z. Monatsh. Chem. 2009, 140, 83
79. For homogeneous redox exchange between stable triarylamine nitrogen centered radical cation and cyanide anion, see: Papouchado, L.; Adams, R. N.; Feldberg, S. W. J. Electroanal. Chem. 1969, 21, 408
80. Fu, Y.; Liu, L.; Yu, H.-Z.; Wang, Y.-M.; Guo, Q.-X. J. Am. Chem. Soc. 2005, 127, 7227
81. Schmittel, M.; Lal, M.; Röck, M.; Langels, A.; Rappoport, Z.; Basheer, A.; Schlirf, J.; Deiseroth, H.-J.; Flörke, U.; Gescheidt, G. Tetrahedron 2009, 65, 10842
82. Opatz, T. Synthesis 2009, 12, 1941
83. Enders, D.; Gerdes, P.; Kippart, H. Angew. Chem. Int. Eng. 1990, 29, 179
84. Roulland, E.; Cecchin, F.; Husson, H.-P. J. Org. Chem. 2005, 70, 4474
85. Wolchenhauer, S. A.; Rychnovsky, S. D. Tetrahedron 2005, 61, 3371
86. Hauser, C. R.; Morris, G. F. J. Org. Chem. 1961, 26, 4740
87. Stork, G.; Jacobson, R. M. Tetrahedron Lett. 1979, 9, 771
88. Juaristi, E.; León-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441
89. Zein, A. L.; Dakhil, O. O.; Dawe, L. N.; Georghiou, P. E. Tetrahedron Lett. 2010, 51, 177
90. Girard, N.; Pouchain, L.; Hurvois, J.-P.; Moinet, C. Synlett 2006, 11, 1679
91. Adriaenssens, L. V.; Austin, C. A.; Gibson, M.; Smith, D.; Hartley, R. C. Eur. J. Org. Chem. 2006, 4998
92. Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784
93. Cola, N.; Mokhtari, N.; Vasse, J.-L.; Szymoniak, J. Org. Lett. 2011, 13, 6292
94. Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1989, 111, 4859
95. Kawagushi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem. 1986, 50, 3107
96. Kametani, T.; Okawara, T. J. Chem. Soc., Perkin Trans. 1 1977, 579
97. Hoffman, H.; Schellenbeck, P. Chem. Ber. 1966, 1134
98. Haynes, R. K.; Au-Yeung, T.-L.; Chan, W.-K.; Lam, W.-L.; Li, Z.-Y.; Yeung, L.-L.; Chan, A. S. C.; Li, P.; Koen, M.; Mitchell, C. R.; Vonwiller, S. C. Eur. J. Org. Chem. 2000, 3205
99. Szawkaøo, J.; Zawadzka, A.; Wojtasiewicz, K.; Leniewski, A.; Drabowicz, J.; Czarnocki, Z. Tetrahedron: Asymmetry 2005, 16, 3619
100. Flack, H. D. Acta Crystallogr. 1983, A39, 876
101. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552
102. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356
103. Dieter, R. K.; Oba, G.; Chandupatla, K. R.; Topping, C. M.; Lu, K.; Watson, R. T. J. Org. Chem. 2004, 69, 3076
104. Dieter, R. K.; Li, S.; Chen, N. J. Org. Chem. 2004, 69, 2867
105. 2 complex, see: Farcasiu, D.; Leu, R.; Ream, P. J. Chem. Soc. Perkin Trans. 2 2001, 427
106. Herath, H. M. T. B.; Nanayakkara, N. P. D. J. Heterocycl. Chem. 2008, 45, 129
107. Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269
108. Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. Synth. Commun. 1999, 29, 1747
109. Beak, P.; Lee, W.-K. J. Org. Chem. 1990, 55, 2578
110. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109
111. Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1998, 63, 6344
112. Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829
113. Appel, R. Angew. Chem., Int. Ed. 1975, 12, 801
114. Liu, L.-X.; Ruan, Y.-P.; Guo, Z.-Q.; Huang, P.-Q. J. Org. Chem. 2004, 69, 6001
115. Chackalamannil, S.; Davies, R. Org. Lett. 2001, 10, 1427
116. Stoll, R. S.; Peters, M. V.; Kuhn, A.; Heiles, S.; Goddard, R.; Bühl, M.; Thiele, C. M.; Hecht, S. J. Am. Chem. Soc. 2009, 131, 357
117. Wang, Y.; Wang, J.; Lin, Y.; Si-Ma, L.-F.; Wang, D.-H.; Chen, L.-G.; Liu, D.-K. Bioorg. Med. Chem. 2011, 21, 4454
118. Barker, G.; OBrien, P.; Campos, K. R. Org. Lett. 2010, 12, 4176
119. Trost, B. M.; Maulide, N.; Livingstone, R. C. J. Am. Chem. Soc. 2008, 130, 16502
120. Bull, J. A.; Charette, A. B. J. Org. Chem. 2008, 73, 8097
121. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, C.; Giacovazzo, C.; Militerni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115
122. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112
123. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837