A divergent approach to 3-piperidinols: A concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 7968-7980

  Archibald, Glenn ^a,b   Lin, Chih Pei ^a,c   Boyd, Peter ^a   Barker, David ^a   Caprio, Vittorio ^a,d  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c MONASH UNIVERSITY   (Australia)

^d MANCHESTER METROPOLITAN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONCISE SYNTHESIS; DIVERGENT APPROACH; ENANTIOPURE; GRIGNARD REAGENT; NUCLEOPHILIC ADDITIONS; ORGANOLITHIUM SPECIES; SWAINSONINE;

CHEMISTRY; ORGANIC COMPOUNDS;

ADDITION REACTIONS;

3 (TERT BUTYLDIPHENYLSILYLOXY) 2 (3' PYRIDYL)PIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 (3',4' DIMETHOXYPHENYL)PIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 ALLYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 BENZYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 ETHYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 ISOPROPYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 METHYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 PHENYLPIPERIDINE; 3 (TERT BUTYLDIPHENYLSILYLOXY) 2 VINYLPIPERIDINE; PIPERIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; SWAINSONINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GRIGNARD REACTION; NUCLEOPHILICITY; SUBSTITUTION REACTION;

MOLECULAR STRUCTURE; PIPERIDINES; QUINOLIZIDINES; STEREOISOMERISM; SWAINSONINE;

EID: 84868095060     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3011914     Document Type: Article

References (139)

1. For recent reviews covering the synthesis of 2-substituted-3- hydroxypiperidines, see: (a) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
2. (b) Winchester, B. G. Tetrahedron: Asymmetry 2009, 20, 645.
3. (c) Davis, B. G. Tetrahedron: Asymmetry 2009, 20, 652.
4. (d) Wijdeven, M. A.; Willemsen, J.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 2831.
5. (a) Koepfli, J. B.; Mead, J. F.; Brockman, J. A. J. Am. Chem. Soc. 1947, 69, 1837.
6. (b) Koepfli, J. B.; Mead, J. F.; Brockman, J. A. J. Am. Chem. Soc. 1949, 71, 1048.
7. (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 495.
8. (b) Yagi, M.; Kouno, T.; Aoyagi, Y.; Murai, H. J. Agric. Chem. Soc. Jpn. 1976, 50, 571.
9. Iminosugars: From Synthesis to Therapeutic Applications; Compain, I.; Martin, O. R., Eds.; Wiley-VCH: Chichester, 2007.
10. (a) Ratle, G.; Monseur, X.; Das, B. C.; Yassi, J.; Khuong-Huu, Q.; Goutarel, R. Bull. Soc. Chem. Fr. 1966, 9, 2945.
11. (b) Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Gouratel, R. Bull. Soc. Chim. Belg. 1972, 81, 425.
12. (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055.
13. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29.
14. For recent reviews covering cycloadditions to nitrones, see: (a) Frederickson, M. Tetrahedron 1997, 53, 403.
15. (b) Broggini, G.; Zecchi, G. Synthesis 1999, 905.
16. (c) de March, P.; Figueredo, M.; Font, J. Heterocycles 1999, 50, 1213.
17. (d) Osborn, H. M. I.; Gemmell, N.; Harwood, L. M. J. Chem. Soc., Perkin Trans. 1 2002, 2419.
18. (e) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585.
19. (f) Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887.
20. (g) Kanemasa, S. Heterocycles 2010, 82, 87.
21. (h) Pinho e Melo, T. M. Pinho e Melo, T. M. V. D. Eur. J. Org. Chem. 2010, 3363.
22. For reviews covering nucleophilic additions to nitrones, see: (a) Lombardo, M.; Trombini, C. Synthesis 2000, 759.
23. (b) Lombardo, M.; Trombini, C. Curr. Org. Chem. 2002, 6, 695.
24. (a) Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772.
25. (b) Riber, D.; Skrydstrup, T. Org. Lett. 2003, 5, 229.
26. (c) Masson, G.; Cividino, P.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2003, 42, 2265.
27. (d) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallée, Y. Synlett 2003, 1527.
28. (e) Johannesen, S. A.; Albu, S.; Hazell, R. G.; Skrydstrup, T. Chem. Commun. 2004, 1962.
29. (f) Zhong, Y.-W.; Xu, M.- H.; Lin, G.-Q. Org. Lett. 2004, 6, 3953.
30. (g) Desvergnes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459.
31. (h) Masson, G.; Philouze, C.; Py, S. Org. Biomol. Chem. 2005, 3, 2067.
32. (i) Cividino, P.; Py, S.; Delair, P.; Greene, A. E. J. Org. Chem. 2007, 72, 485.
33. (j) Desvergnes, S.; Desvergnes, V.; Martin, O. R.; Itoh, K.; Liu, H.-W.; Py, S. Bioorg. Med. Chem. 2007, 15, 6443.
34. (k) Burchak, O. N.; Philouze, C.; Chavant, P. Y.; Py, S. Org. Lett. 2008, 10, 3021.
35. (l) Rehák, J.; Fišera, L.; Podolan, G.; Koz?íšek, J.; Perašínová, L. Synlett 2008, 1260.
36. (m) Burchak, O. N.; Py, S. Tetrahedron 2009, 65, 7333.
37. (n) Wu, S.-F.; Zheng, X.; Ruan, Y.- P.; Huang, P.-Q. Org. Biomol. Chem. 2009, 7, 2967.
38. (o) Wu, S.-F.; Ruan, Y.-P.; Zheng, X.; Huang, P.-Q. Tetrahedron 2010, 66, 1653.
39. (p) Burchak, O. N.; Masson, G.; Py, S. Synlett 2010, 1623.
40. (a) Gössinger, E. Monatsh. Chem. 1982, 113, 495.
41. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbuch, M.-T.; Pierre, J.-L. Tetrahedron Lett. 1998, 39, 2565.
42. (c) Peer, A.; Vasella, A. Helv. Chim. Acta 1999, 82, 1044.
43. (d) Berge, J. M.; Copley, R. C. B.; Eggleston, D. S.; Hamprecht, D. W.; Jarvest, R. L.; Mensah, L. M.; O'Hanlon, P. J.; Pope, A. Bioog. Med. Chem. Lett. 2000, 10, 1811.
44. (e) Eriksson, C.; Sjödin, K.; Schlyter, F.; Högberg, H.-E. Tetrahedron: Asymmetry 2006, 17, 1074.
45. (f) Chan, T.-H.; Chang, Y.-F.; Hsu, J.-J.; Cheng, W.-C. Eur. J. Org. Chem. 2010, 5555.
46. (a) Gössinger, E. Tetrahedron Lett. 1980, 21, 2229.
47. (b) Gössinger, E. Monatsh. Chem. 1981, 112, 1017.
48. (c) Lathbury, D.; Gallagher, T. Tetrahedron Lett. 1985, 26, 6249.
49. (d) Tufariello, J. J.; Puglis, J. M. Tetrahedron Lett. 1986, 27, 1489.
50. (e) Adams, D. R.; Carruthers, W.; Williams, M. J.; Crowley, P. J. J. Chem. Soc., Perkin Trans. 1 1989, 1507.
51. (f) Grigg, R.; Hadjisoteriou, M.; Kennewell, P.; Markandu, J. J. Chem. Soc. Chem. Commun. 1992, 1537.
52. (g) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211.
53. (h) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467.
54. (i) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203.
55. (j) Chackalamannil, S.; Davies, R. J.; Wang, Y.; Asberom, T.; Doller, D.; Wong, J.; Leone, D.; McPhail, A. T. J. Org. Chem. 1999, 64, 1932.
56. (k) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900.
57. (l) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 953.
58. (m) Kikuchi, H.; Tasaka, H.; Hirai, S.; Takaya, Y.; Iwabuchi, Y.; Ooi, H.; Hatakeyama, S.; Kim, H.- S.; Wataya, N Y.; Oshima, Y. J. Med. Chem. 2002, 45, 2563.
59. (n) Brandi, A.; Cicchi, S.; Paschetta, V.; Gomez Pardo, D.; Cossy, J. Tetrahedron Lett. 2002, 43, 9357.
60. (o) Alsbaiee, A.; Ali, S. A. Tetrahedron 2008, 64, 6635.
61. (p) Moosa, B. A.; Ali, S. A. Tetrahedron 2009, 65, 8231.
62. For the most recent reviews covering the reactions of chiral pyrroline N-oxides, see: (a) Revuelta, J.; Cicchi, S.; Goti, A.; Brandi, A. Synthesis 2007, 485.
63. (b) Pellissier, H. Tetrahedron 2007, 63, 3235.
64. Ashoorzadeh, A.; Archibald, G.; Caprio, V. Tetrahedron 2009, 65, 4671.
65. Soai, K.; Ookawa, A. J. Org. Chem. 1986, 51, 4000.
66. Ikunaka, M.; Matsumoto, J.; Fujima, Y.; Hirayama, Y. Org. Process Res. Dev. 2002, 6, 49.
67. Yamakawa, T.; Masaki, M.; Nohira, H. Bull. Chem. Soc. Jpn. 1991, 64, 2730.
68. Ali, S. A. Tetrahedron Lett. 1993, 34, 5325.
69. Goti, A.; De Sarlo, F.; Romani, M. Tetrahedron Lett. 1994, 35, 6571.
70. Cicchi, S.; Marradi, M.; Goti, A.; Brandi, A. Tetrahedron Lett. 2001, 42, 6503.
71. Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743.
72. Seeman, J. I. Chem. Rev. 1983, 83, 83.
73. Thesing, J.; Mayer, H. Chem. Ber. 1956, 89, 2159.
74. Cai, D.; Larsen, R. D.; Reider, P. J. Tetrahedron Lett. 2002, 43, 4285.
75. Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349.
76. Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773.
77. Pulz, R.; Cicchi, S.; Brandi, A.; Reissig, H.-U. Eur. J. Org. Chem. 2003, 1153.
78. Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Synlett 2002, 817.
79. (a) Pulz, R.; Watanabe, T.; Schade, W.; Reissig, H.-U. Synlett 2000, 983.
80. (b) Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Org. Lett. 2002, 4, 2353.
81. (a) Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353.
82. (b) Merino, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
83. Liu, L.-X.; Ruan, Y.-P.; Guo, Z.-Q.; Huang, P.-Q. J. Org. Chem. 2004, 69, 6001.
84. (a) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
85. (b) Huang, P.-Q.; Wei, B.-G.; Ruan, Y.-P. Synlett 2003, 1663.
86. (c) Emmanuvel, L.; Kamble, D. A.; Sudalai, A. Tetrahedron: Asymmetry 2009, 20, 84.
87. (a) Déchamps, I.; Pardo, D. G.; Cossy, J. Tetrahedron 2007, 63, 9082.
88. (b) Bates, R. W.; Dewy, M. R. Org. Lett. 2009, 11, 3706.
89. For synthetic routes to (+)-swainsonine, see: (a) Oishi, T.; Iwakuma, T.; Hirama, M.; Itô, S. Synlett 1995, 404.
90. (b) Davis, B.; Bell, A. A.; Nash, R. J.; Watson, A. A.; Griffiths, R. C.; Jones, M. G.; Smith, C.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8565.
91. (c) Guo, H.; O'Doherty, G. A. Org. Lett. 2006, 8, 1609.
92. (d) Guo, H.; O'Doherty, G. A. Tetrahedron 2008, 64, 304.
93. (e) Håkansson, A. E.; van Ameijde, J.; Horne, G.; Nash, R. J.; Wormald, M. R.; Kato, A.; Besra, G. S.; Gurcha, S.; Fleet, G. W. J. Tetrahedron Lett. 2008, 49, 179.
94. (f) Alam, M. A.; Kumar, A.; Vankar, Y. D. Eur. J. Org. Chem. 2008, 4972.
95. (g) Chen, M.-J.; Tsai, Y.-M. Tetrahedron 2011, 67, 1564.
96. (h) Chooprayoon, S.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Org. Biomol. Chem. 2011, 9, 531.
97. (a) Mukai, C.; Sugimoto, Y.-i.; Miyazawa, K.; Yamaguchi, S.; Hanaoka, M. J. Org. Chem. 1998, 63, 6281.
98. (b) de Vicente, J.; Arrayás, R. G.; Cañada, J.; Carretero, J. C. Synlett 2000, 53.
99. (c) Buschmann, N.; Rückert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325.
100. (d) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774.
101. (e) Ceccon, J.; Greene, A. E.; Poisson, J. F. Org. Lett. 2006, 8, 4739.
102. (f) Kwon, H. Y.; Park, C. M.; Lee, S. B.; Youn, J. H.; Kang, S. H. Chem.-Eur. J. 2008, 14, 1023.
103. For example, see: (a) Campos, K. R.; Cai, D.; Journet, M.; Kowal, J. J.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2001, 66, 3634.
104. (b) Campos, K. R.; Journet, M.; Cai, D.; Kowal, J. J.; Lee, S.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2003, 68, 2338.
105. For a previous example, see: Xu, Q.; Rozners, E. Org. Lett. 2005, 7, 2821.
106. Fitch, R. W.; Garraffo, H. M.; Spande, T. F.; Yeh, H. J. C.; Daly, J. W. J. Nat. Prod. 2003, 66, 1345.
107. For synthetic routes to epiquinamide, see: (a) Wijdeven, M. A.; Botman, P. N. M.; Wijtmans, R.; Schoemaker, H. E.; Rutjes, F. P. J. T.; Blaauw, R. H. Org. Lett. 2005, 7, 4005.
108. (b) Kanakubo, A.; Gray, D.; Innocent, N.; Wonnacott, S.; Gallagher, T. Bioorg. Med. Chem. Lett. 2006, 16, 4648.
109. (c) Suyama, T. L.; Gerwick, W. H. Org. Lett. 2006, 8, 4541.
110. (d) Huang, P.-Q.; Guo, Z.-Q.; Ruan, Y.-P. Org. Lett. 2006, 8, 1435.
111. (e) Tong, S. T.; Barker, D. Tetrahedron Lett. 2006, 47, 5017.
112. (f) Voituriez, A.; Ferreira, F.; Pérez-Luna, A.; Chemla, F. Org. Lett. 2007, 9, 4705.
113. (g) Wijdeven, M. A.; Wijtmans, R.; van den Berg, R. J. F.; Noorduin, W.; Schoemaker, H. E.; Sonke, T.; van Delft, F. L.; Blaauw, R. H.; Fitch, R. W.; Spande, T. F.; Daly, J. W.; Rutjes, F. P. J. T. Org. Lett. 2008, 10, 4001.
114. (h) Airiau, E.; Spangenberg, T.; Girard, N.; Breit, B.; Mann, A. Org. Lett. 2010, 12, 528.
115. (i) Chandrasekhar, S.; Parida, B. B.; Rambabu, C. Tetrahedron Lett. 2009, 50, 3294.
116. (j) Fitch, R. W.; Saturgeon, G. D.; Patel, S. R.; Spande, T. F.; Garraffo, H. M.; Daly, J. W.; Blaauw, R. H. J. Nat. Prod. 2009, 72, 243.
117. (k) Ghosh, S.; Shashidhar, J. Tetrahedron Lett. 2009, 50, 1177.
118. (l) Srivastava, A. K.; Das, S. K.; Panda, G. Tetrahedron 2009, 65, 5322.
119. (m) Tuan, L. A.; Pyeon, H.; Kim, G. Tetrahedron Lett. 2010, 51, 157.
120. (n) Santos, L. S.; Mirabal-Gallardo, Y.; Shankaraiah, N.; Simirgiotis, M. J. Synthesis 2011, 51.
121. Couch, J. F. J. Am. Chem. Soc. 1934, 56, 2434.
122. For synthetic routes to lupinine, see: (a) Leonard, N. J.; Conrow, K.; Fulmer, R. W. J. Org. Chem. 1957, 22, 1445.
123. (b) Goldberg, S. I.; Ragade, I. J. Org. Chem. 1967, 32, 1046.
124. (c) Okita, M.; Wakamatsu, T.; Ban, Y. Heterocycles 1983, 20, 401.
125. (d) Takahata, H.; Yamabe, K.; Suzuki, T.; Yamazaki, T. Chem. Pharm. Bull. 1986, 34, 4523.
126. (e) Haddad, M.; Célérier, J.-P.; Lhommet, G. Heterocycles 1987, 26, 2335.
127. (f) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325.
128. (g) Morley, C.; Knight, D. W.; Share, A. C. Tetrahedron: Asymmetry 1990, 1, 147.
129. (h) Hua, D. H.; Miao, S. W.; Bravo, A. A.; Takemoto, D. J. Synthesis 1991, 970.
130. (i) Paulvannan, K.; Schwarz, J. B.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215.
131. (j) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732.
132. (k) Wanner, M. J.; Koomen, G.-J. J. Org. Chem. 1996, 61, 5581.
133. (l) Mangeney, P.; Hamon, L.; Raussou, S.; Urbain, N.; Alexakis, A. Tetrahedron 1998, 54, 10349.
134. (m) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 2000, 65, 2368.
135. (n) Agami, C.; Dechoux, L.; Hebbe, S.; Ménard, C. Tetrahedron 2004, 60, 5433.
136. (o) Ma, S.; Ni, B. Chem.-Eur. J. 2004, 10, 3286.
137. (p) Chang, M.-Y.; Tai, H.-M.; Lin, C.-H.; Chang, N.-C. Heterocycles 2005, 65, 395.
138. (q) Pohmakotr, M.; Seubsai, A.; Numeechai, P.; Tuchinda, P. Synthesis 2008, 1733.
139. Saito, K.; Yoshino, T.; Tsai, S.; Ohmiya, S.; Kubo, H.; Otomasu, H.; Murakoshi, I. Chem. Pharm. Bull. 1987, 35, 1308.