Asymmetric and enantiospecific syntheses of 1-hydroxymethyl pyrrolizidine alkaloids

Tetrahedron Asymmetry

Volumn 25, Issue 5, 2014, Pages 387-403

  Brambilla, Marta ^a   Davies, Stephen G ^a   Fletcher, Ai M ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ISORETRONECANOL; MOLECULAR SCAFFOLD; PROLINE DERIVATIVE; PYRROLIZIDINE ALKALOID; RADICAL; TRACHELANTAMIDINE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CLAISEN REARRANGEMENT; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGENATION; HYDROXYLATION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; RADICAL REACTION;

EID: 84897147241     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2014.02.001     Document Type: Review

References (125)

1. P.A. Searle, and T.F. Molinski J. Org. Chem. 58 1993 7578
2. D.H. Rich Peptidase Inhibitors in Comprehensive Medicinal Chemistry P.G. Sammes, Vol. 2 1990 Pergamon Press Oxford 391
3. P.W.K. Woo Tetrahedron Lett. 26 1985 2973
4. S. Kano, T. Yokomatsu, H. Iwasawa, and S. Shibuya Chem. Lett. 16 1987 1531
5. J. Maibaum, and D.H. Rich J. Org. Chem. 53 1988 869
6. R.M. Devant, and H.E. Radunz Tetrahedron Lett. 29 1988 2307
7. N. Asano, H. Kuroi, K. Ikeda, H. Kizu, Y. Kameda, A. Kato, I. Adachi, A.A. Watson, R.J. Nash, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1
8. I. Pastuszak, R.J. Molyneux, L.F. James, and A.D. Elbein Biochemistry 29 1990 1886
9. R. De la Vega, M.P. Gutierrez, C. Sanz, R. Calvo, L.M. Robredo, C. De la Cuadra, and M. Muzquiz Ind. Crops Prod. 5 1996 141
10. R. Adams, and E.F. Rogers J. Am. Chem. Soc. 61 1942 2815
11. R. Adams, and K.E. Hamlin Jr. J. Am. Chem. Soc. 64 1942 2597
12. A.S. Labenskii, and G.P. Men'shikov Zh. Obshch. Khim. 18 1948 1836
13. C.C.J. Culvenor, and L.W. Smith Aust. J. Chem. 20 1967 2499
14. G.P. Men'shikov, and G.M. Borodina Zh. Obshch. Khim. 11 1941 209
15. Y. Tsuda, and L. Marion Can. J. Chem. 41 1963 1919
16. F. Galinovsky, H. Goldberger, and M. Pohm Monatsh. Chem. 80 1949 550
17. T. Hartmann, and L. Witte S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives Vol. 9 1995 Pergamon Press New York 155
18. V.S. Konovalov, and G.P. Men'shikov Zh. Obshch. Khim. 15 1945 328
19. H.L. De Waal Nature 146 1940 777
20. A.P. Orekhov, R. Konovalova, and V. Tiedebel Ber. Dtsch. Chem. Ges. 68B 1935 1886
21. G.P. Men'shikov, S.O. Denisova, and P.S. Massagetov Zh. Obshch. Khim. 22 1952 1509
22. R.S. Sawhney, C.K. Atal, C.C.J. Culvenor, and L.W. Smith Aust. J. Chem. 27 1974 1805
23. K. Yamada, H. Tatematsu, R. Unno, Y. Hirata, and I. Hirono Tetrahedron. Lett. 46 1978 4543
24. A. Danilova, L. Utkin, and P. Massagetov Zh. Obshch. Khim. 25 1955 831
25. O. Were, M. Benn, and R.M. Munavu J. Nat. Prod. 54 1991 491
26. A specific rotation for 18 was not reported, see: J.C.M. Medina, G.F. Gauze, G.J. Vidotti, M.H. Sarragiotto, E.A. Basso, and J.L.B. Peixoto Tetrahedron Lett. 50 2009 2640
27. T. Hartmann, and L. Witte S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives Vol. 9 1995 Pergamon Oxford 155
28. For example; P.P. Fu, Q. Xia, G. Lin, and M.W. Chou Drug Metab. Rev. 36 2004 1
29. M.J. Stewart, and V. Steenkamp Ther. Drug Monit. 23 2001 698
30. D.J. Robins Nat. Prod. Rep. 12 1995 413
31. J.L. Hartwell Cancer Treat. Rep. 60 1976 1031
32. L.W. Smith, and C.C.J. Culvenor J. Nat. Prod. 44 1981 129
33. For another review, see: J.A. Vanecko, and F.G. West Heterocycles 74 2007 125
34. J. Schnekenburger, and H. Vollhardt Arch. Pharm. 310 1977 177
35. For reviews, see: S.G. Davies, A.D. Smith, and P.D. Price Tetrahedron: Asymmetry 16 2005 2833
36. S.G. Davies, A.M. Fletcher, P.M. Roberts, and J.E. Thomson Tetrahedron: Asymmetry 23 2012 1111
37. S.G. Davies, and I.A.S. Walters J. Chem. Soc.; Perkin Trans. 1 1994 1129
38. S.G. Davies, E.M. Foster, C.R. McIntosh, P.M. Roberts, T.E. Rosser, A.D. Smith, and J.E. Thomson Tetrahedron: Asymmetry 22 2011 1035
39. C. Aciro, T.D.W. Claridge, S.G. Davies, P.M. Roberts, A.J. Russell, and J.E. Thomson Org. Biomol. Chem. 6 2008 3751
40. C. Aciro, S.G. Davies, P.M. Roberts, A.J. Russell, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 6 2008 3762
41. C.W. Bond, A.J. Cresswell, S.G. Davies, W. Kurosawa, J.A. Lee, A.M. Fletcher, P.M. Roberts, A.J. Russell, A.D. Smith, and J.E. Thomson J. Org. Chem. 74 2009 6735
42. M.B. Brennan, T.D.W. Claridge, R.G. Compton, S.G. Davies, A.M. Fletcher, M.C. Henstridge, D.S. Hewings, W. Kurosawa, J.A. Lee, P.M. Roberts, A.K. Schoonen, and J.E. Thomson J. Org. Chem. 77 2012 7241
43. M. Brambilla, S.G. Davies, A.M. Fletcher, P.M. Roberts, and J.E. Thomson Tetrahedron 70 2014 204
44. Y. Nagao, W.-M. Dai, M. Ochiai, S. Tsukagoshi, and E. Fujita J. Am. Chem. Soc. 110 1988 289
45. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127
46. S.G. Davies, and H.J. Sanganee Tetrahedron: Asymmetry 6 1995 671
47. S.D. Bull, S.G. Davies, R.L. Nicholson, H.J. Sanganee, and A.D. Smith Org. Biomol. Chem. 1 2003 2886
48. S.D. Bull, S.G. Davies, S. Jones, M.E.C. Polywka, R.S. Prasad, and H.J. Sanganee Synlett 1998 519
49. Y. Nagao, W.-M. Dai, M. Ochiai, and M. Shiro Tetrahedron 46 1990 6361
50. Y. Nagao, W.-M. Dai, M. Ochiai, S. Tsukagoshi, and E. Fujita J. Org. Chem. 55 1990 1148
51. E. Pereira, C. Alves, F. de, M.A. Böckelmann, and R.A. Pilli Quim. Nova 31 2008 771
52. E. Pereira, C.F. de Alves, M.A. Böckelmann, and R.A. Pilli Tetrahedron Lett. 46 2005 2691
53. F.A. Davis, and B.-C. Chen Chem. Soc. Rev. 27 1998 13
54. P. Zhou, B.-C. Chen, and F.A. Davis Tetrahedron 60 2004 8003
55. J.A. Ellman, T.D. Owens, and T.P. Tang Acc. Chem. Res. 35 2002 984
56. S. Ishikawa, F. Noguchi, and A. Kamimura J. Org. Chem. 75 2010 3578
57. Y. Arai, T. Kontani, and T. Koizumi Chem. Lett. 20 1991 2135
58. Y. Arai, T. Kontani, and T. Koizumi J. Chem. Soc.; Perkin Trans. 1 1994 15
59. S. Bertrand, N. Hoffmann, and J.-P. Pete Tetrahedron Lett. 40 1999 3173
60. S. Bertrand, N. Hoffmann, and J.-P. Pete Eur. J. Org. Chem. 2000 2227
61. X. Han, F. Zhong, Y. Wang, and Y. Lu Angew. Chem.; Int. Ed. 51 2012 767
62. H. Konno, M. Kishi, K. Hiroya, and K. Ogasawara Heterocycles 49 1998 33
63. K. Hiroya, Y. Kurihara, and K. Ogasawara Angew. Chem.; Int. Ed. 34 1995 2287
64. S. Takano, N. Ogawa, and K. Ogasawara Heterocycles 16 1981 915
65. R.K. Dieter, N. Chen, and R.T. Watson Tetrahedron 61 2005 3221
66. P. Beak, S.T. Kerrick, S. Wu, and J. Chu J. Am. Chem. Soc. 116 1994 3231
67. G. Haviari, J.-P. Célérier, H. Petit, and G. Lhommet Tetrahedron Lett. 34 1993 1599
68. O. David, J. Blot, C. Bellec, M.-C. Fargeau-Bellassoued, G. Haviari, J.-P. Célérier, G. Lhommet, J.-C. Gramain, and D. Gardette J. Org. Chem. 64 1999 3122
69. S. Ledoux, E. Marchalant, J.-P. Célérier, and G. Lhommet Tetrahedron Lett. 42 2001 5397
70. For example, see: K.K.S. Reddy, B.V. Rao, and S.S. Raju Tetrahedron: Asymmetry 22 2011 662
71. D.J. Robins, and S. Sakdarat J. Chem. Soc.; Chem. Commun. 1979 1181
72. D.J. Robins, and S. Sakdarat J. Chem. Soc.; Perkin Trans. 1 1981 909
73. H. Rüeger, and M. Benn Heterocycles 19 1982 1677
74. T. Moriwake, S. Hamano, and S. Saito Heterocycles 27 1988 1135
75. D.W. Knight, and A.C. Share Gazz. Chim. Ital. 121 1991 49
76. D.W. Knight, A.C. Share, and P.T. Gallagher J. Chem. Soc.; Perkin Trans. 1 1991 1615
77. D.W. Knight, A.C. Share, and P.T. Gallagher J. Chem. Soc.; Perkin Trans. 1 1997 2089
78. R.S. Jolly, and T. Livinghouse J. Am. Chem. Soc. 110 1988 7536
79. K.A. Parker, and R. O'Fee J. Am. Chem. Soc. 105 1983 654
80. M. Ikeda, H. Teranishi, N. Iwamura, and H. Ishibashi Heterocycles 45 1997 863
81. J.A. Seijas, M.P. Vázquez-Tato, L. Castedo, R.J. Estévez, M.G. Ónega, and M. Ruiz Tetrahedron 48 1992 1637
82. H. Ishibashi, M. Sasaki, and T. Taniguchi Tetrahedron 64 2008 7771
83. H. Ishibashi, H. Ozeki, and M. Ikeda J. Chem. Soc.; Chem. Commun. 1986 654
84. T. Sato, K. Tsujimoto, K. Matsubayashi, K. Ishibashi, and M. Ikeda Chem. Pharm. Bull. 40 1992 2308
85. H. Ishibashi, N. Uemura, H. Nakatani, M. Okazaki, T. Sato, N. Nakamura, and M. Ikeda J. Org. Chem. 58 1993 2360
86. S. Le Coz, A. Mann, F. Thareau, and M. Taddei Heterocycles 36 1993 2073
87. D. Craig, C.J.T. Hyland, and S.E. Ward Chem. Commun. 2005 3439
88. D. Craig, C.J.T. Hyland, and S.E. Ward Synlett 2006 2142
89. J.G. Knight, and S.V. Ley Tetrahedron Lett. 32 1991 7119
90. S.V. Ley Pure Appl. Chem. 66 1994 1415
91. T.W. Kwon, P.F. Keusenkothen, and M.B. Smith J. Org. Chem. 57 1992 6169
92. P.F. Keusenkothen, and M.B. Smith J. Chem. Soc.; Perkin Trans. 1 1994 2485
93. P.-O. Delaye, T.K. Pradhan, E. Lambert, J.-L. Vasse, and J. Szymoniak Eur. J. Org. Chem. 2010 3395
94. K. Tatsuta, H. Takahashi, Y. Amemiya, and M. Kinoshita J. Am. Chem. Soc. 105 1983 4096
95. K. Tatsuta, S. Miyashita, K. Akimoto, and M. Kinoshita Bull. Chem. Soc. Jpn. 55 1982 3254
96. A.J. Aasen, and C.C. Culvenor J. Org. Chem. 34 1969 4143
97. J. Mulzer, and M. Scharp Synthesis 1993 615
98. S.E. Denmark, and A. Thorarensen J. Org. Chem. 59 1994 5672
99. S.E. Denmark, D.L. Parker Jr.; and J.A. Dixon J. Org. Chem. 62 1997 435
100. S.E. Denmark, A. Thorarensen, and D.S. Middleton J. Org. Chem. 60 1995 3574
101. S.E. Denmark, A. Thorarensen, and D.S. Middleton J. Am. Chem. Soc. 118 1996 8266
102. S.E. Denmark, and A.R. Hurd J. Org. Chem. 63 1998 3045
103. D. Ma, and J. Zhang J. Chem. Soc.; Perkin Trans. 1 1999 1703
104. A.R. Chamberlin, and J.Y.L. Chung J. Am. Chem. Soc. 105 1983 3653
105. A.R. Chamberlin, and J.Y.L. Chung J. Org. Chem. 50 1985 4425
106. R.A. Pilli, and D. Russowsky J. Org. Chem. 61 1996 3187
107. J.-K. Choi, and D.J. Hart Tetrahedron 41 1985 3959
108. D.J. Hart, and T.-K. Yang J. Org. Chem. 50 1985 235
109. D.J. Hart, and T.-K. Yang Chem. Commun. 1983 135
110. A. Goti, S. Cicchi, M. Cacciarini, F. Cardona, V. Fedi, and A. Brandi Eur. J. Org. Chem. 2000 3633
111. A. Goti, M. Cacciarini, F. Cardona, F.M. Cordero, and A. Brandi Org. Lett. 3 2001 1367
112. A. Goti, S. Cicchi, F.M. Cordero, V. Fedi, and A. Brandi Molecules 4 1999 1
113. S. Akai, K. Tanimoto, Y. Kanao, S. Omura, and Y. Kita Chem. Commun. 2005 2369
114. H. Nemoto, K. Tanimoto, Y. Kanao, S. Omura, Y. Kita, and S. Akai Tetrahedron 68 2012 7295
115. S.H. Kang, G.T. Kim, and Y.S. Yoo Tetrahedron Lett. 38 1997 603
116. J.-B. Ahn, C.-S. Yun, K.H. Kim, and D.-C. Ha J. Org. Chem. 65 2000 9249
117. H. Ito, Y. Ikeuchi, T. Taguchi, Y. Hanzawa, and M. Shiro J. Am. Chem. Soc. 116 1994 5469
118. J. Mulzer, and M. Shanyoor Tetrahedron Lett. 34 1993 6545
119. T. Moriwake, S. Hamano, D. Miki, S. Saito, and S. Torii Chem. Lett. 15 1986 815
120. K.N. Houk, M.N. Paddon-Row, N.G. Rondan, Y.-D. Wu, F.K. Brown, D.C. Spellmeyer, J.T. Metz, Y. Li, and R.J. Loncharich Science 231 1986 1108
121. G.W.J. Fleet, J.A. Seijas, and M.P. Vázquez-Tato Tetrahedron 47 1991 525
122. G.W.J. Fleet, J.M. Peach, P.W. Smith, G.N. Austin, P.D. Baird, and D.J. Watkin Tetrahedron 43 1987 3095
123. K. Hashimura, S. Tomita, K. Hiroya, and K. Ogasawara J. Chem. Soc.; Chem. Commun. 1995 2291
124. A.G.H. Wee Tetrahedron Lett. 41 2000 9025
125. A.G.H. Wee J. Org. Chem. 66 2001 8513