SmI 2-mediated carbonyl-alkene couplings for the synthesis of small carbocyclic rings

Synlett

Volumn , Issue 1, 2012, Pages 6-20

  Harb, Hassan Y ^a   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

cyclization; natural product synthesis; radical reactions; samarium diiodide; small rings

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; DITERPENOID; HEMPA; KETONE; LACTONE; NATURAL PRODUCT; PESTALOTIOPSIN A; SAMARIUM DIIODIDE; SILANE DERIVATIVE; SILICON; STOLONIDIOL; TAEDOLIDOL; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; CYCLIZATION; DIASTEREOISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84655162272     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290093     Document Type: Article

References (88)

1. Donaldson W A., Tetrahedron 2001 57 8589
2. Sergeiko A, Poroikov V V., Hanus L O., Dembitsky V M., Open Med. Chem. J. 2008 2 26
3. Selected reviews:, Bach T, Hehn J, Angew. Chem. Int. Ed. 2011 50 1000
4. Iriondo-Alberdi J, Greaney M F., Eur. J. Org. Chem. 2007 4801
5. Crimmins M T., Chem. Rev. 1988 88 1453
6. Walton J C., Top. Curr. Chem. 2006 264 163
7. Jung M E., Marquez R, Tetrahedron Lett. 1997 38 6521
8. Jung M E., Trifunovich I D., Lensen N, Tetrahedron Lett. 1992 33 6719
9. Fernández-Mateos A, MartindelaNava E, PascualCoca G, RamosSilva A, RubioGonzález R, Org. Lett. 1999 1 607
10. Gansäuer A, Lauterbach T, Geich-Gimbel D, Chem. Eur. J. 2004 10 4983
11. Friedrich J, Walczak K, Dolg M, Piestert F, Lauterbach T, Worgull D, Gansäuer A, J. Am. Chem. Soc. 2008 130 1788
12. Gansäuer A, Worgull D, Knebel K, Huth I, Schnakenburg G, Angew. Chem. Int. Ed. 2009 48 8882
13. Gansäuer A, Greb A, Huth I, Worgull D, Knebel K, Tetrahedron 2009 65 10791
14. Elphimoff-Felkin I, Sarda P, Tetrahedron Lett. 1983 24 4425; and references cited therein
15. Corey E J., Wu Y.-J, J. Am. Chem. Soc. 1993 115 8871
16. Aurrecoechea J M., Lopez B, Arrate M, J. Org. Chem. 2000 65 6493
17. McAuley B J., Nieuwenhuyzen M, Sheldrake G N., Org. Lett. 2000 2 1457
18. Namy J L., Girard P, Kagan H B., Nouv. J. Chim. 1977 1 5
19. Girard P, Namy J L., Kagan H B., J. Am. Chem. Soc. 1980 102 2693
20. For recent reviews on the use of samarium(II) iodide, see:, Procter D J., Flowers R A. II., Skrydstrup T, Organic Synthesis Using Samarium Diiodide: A Practical Guide RSC Publishing Cambridge 2010
21. Nicolaou K C., Ellery S P., Chen J S., Angew. Chem. Int. Ed. 2009 48 7140
22. Gopalaiah K, Kagan H B., New J. Chem. 2008 32 607
23. Edmonds D J., Johnston D, Procter D J., Chem. Rev. 2004 104 3371
24. Dahlén A, Hilmersson G, Eur. J. Inorg. Chem. 2004 3393
25. Kagan H B., Tetrahedron 2003 59 10351
26. Steel P G., J. Chem. Soc., Perkin Trans. 1 2001 2727
27. Kagan H, Namy J L., In Lanthanides: Chemistry and Use in Organic Synthesis Kobayashi S Springer Berlin 1999 155
28. Molander G A., Harris C R., Tetrahedron 1998 54 3321
29. Szostak M, Procter D J., Angew. Chem. Int. Ed. 2011 50 7737
30. 2-mediated cascade reactions from our group, see:, Coote S C., Quenum S, Procter D J., Org. Biomol. Chem. 2011 9 5104
31. Findley T J. K., Sucunza D, Miller L C., Helm M D., Helliwell M, Davies D T., Procter D J., Org. Biomol. Chem. 2011 9 2433
32. Helm M D., Da Silva M, Sucunza D, Findley T J. K., Procter D J., Angew. Chem. Int. Ed. 2009 48 9315
33. Helm M D., Da Silva M, Sucunza D, Helliwell M, Procter D J., Tetrahedron 2009 65 10816
34. Helm M D., Sucunza D, Da Silva M, Helliwell M, Procter D J., Tetrahedron Lett. 2009 50 3224; see also ref. 29d and 31a
35. Weinges K, Schmidbauer S B., Schick H, Chem. Ber. 1994 127 1305
36. Molander G A., McKie J A., J. Org. Chem. 1992 57 3132
37. Shabangi M, Flowers R A. II., Tetrahedron Lett. 1997 38 1137
38. Shotwell J B., Sealy J M., Flowers R A. II., J. Org. Chem. 1999 64 5251
39. Sadasivam D V., Antharjanam P K. S., Prasad E, Flowers R A. II., J. Am. Chem. Soc. 2008 130 7228
40. Chopade P, Prasad E, Flowers R A. II., J. Am. Chem. Soc. 2004 126 44
41. Dahlén A, Hilmersson G, Tetrahedron Lett. 2001 42 5565; see also ref. 29
42. Johnston D, McCusker C M., Procter D J., Tetrahedron Lett. 1999 40 4913
43. Johnston D, McCusker C F., Muir K, Procter D J., J. Chem. Soc., Perkin Trans. 1 2000 681
44. Park S.-U, Varick T R., Newcomb M, Tetrahedron Lett. 1990 31 2975
45. Jung M E., Marquez R, Houk K N., Tetrahedron Lett. 1999 40 2661
46. Fossey J, Lefort D, Sorba J, Free Radicals in Organic Chemistry John Wiley and Sons Chichester 1995
47. Curran D P., Fevig T L., Jasperse C P., Totleben M J., Synlett 1992 943; see also ref. 8a
48. Viehe H G., Janousek Z, Merényi R, Acc. Chem. Res. 1985 18 148
49. Johnston D, Francon N, Edmonds D J., Procter D J., Org. Lett. 2001 3 2001
50. Johnston D, Couche E, Edmonds D J., Muir K W., Procter D J., Org. Biomol. Chem. 2003 1 328
51. Molander G A., Harris C R., Chem. Rev. 1996 96 307
52. Beckwith A L. J., Tetrahedron 1981 37 3073
53. Ohno H, Okumura M, Maeda S.-i, Iwasaki H, Wakayama R, Tanaka T, J. Org. Chem. 2003 68 7722
54. Williams D B. G., Blann K, Eur. J. Org. Chem. 2004 3286
55. Williams D B. G., Caddy J, Blann K, Grové J J. C., Holzapfel C W., Synthesis 2009 2009
56. Yang H, Drain R L., Franco C A., Clark J M., Antiviral Res. 1996 29 233
57. Hutton T K., Muir K, Procter D J., Org. Lett. 2002 4 2345
58. Hutton T K., Muir K W., Procter D J., Org. Lett. 2003 5 4811
59. Upadhyay S K., Hoz S, J. Org. Chem. 2011 76 1355
60. Amiel-Levy M, Hoz S, J. Am. Chem. Soc. 2009 131 8280
61. Guazzelli G, Duffy L A., Procter D J., Org. Lett. 2008 10 4291
62. Duffy L A., Matsubara H, Procter D J., J. Am. Chem. Soc. 2008 130 1136
63. Guazzelli G, De Grazia S, Collins K D., Matsubara H, Spain M, Procter D J., J. Am. Chem. Soc. 2009 131 7214
64. Parmar D, Duffy L A., Sadasivam D V., Matsubara H, Bradley P A., Flowers R A. II., Procter D J., J. Am. Chem. Soc. 2009 131 15467
65. Collins K D., Oliveira J M., Guazzelli G, Sautier B, De Grazia S, Matsubara H, Helliwell M, Procter D J., Chem. Eur. J. 2010 16 10240
66. Parmar D, Price K, Spain M, Matsubara H, Bradley P A., Procter D J., J. Am. Chem. Soc. 2011 133 2418
67. Szostak M, Spain M, Procter D J., Chem. Commun. 2011 47 10254
68. Szostak M, Spain M, Parmar D, Procter D J., Chem. Commun. 2011 in press; DOI 10.1039/c1cc14252f
69. Mori K, Iguchi K, Yamada N, Yamada Y, Inouye Y, Tetrahedron Lett. 1987 28 5673
70. Baker T M., Sloan L A., Choudhury L H., Murai M, Procter D J., Tetrahedron: Asymmetry 2010 21 1246
71. Sloan L A., Baker T M., Macdonald S J. F., Procter D J., Synlett 2007 3155
72. Bezzenine-Lafolée S, Guibé F, Villar H, Zriba R, Tetrahedron 2004 60 6931
73. Zriba R, Bezzenine-Lafolée S, Guibé F, Magnier-Bouvier C, Tetrahedron Lett. 2007 48 8234
74. Zriba R, Bezzenine-Lafollée S, Guibé F, Guillerez M.-G, Synlett 2005 2362
75. Martin-Fontecha M, Agarrabeitia A R., Ortiz M J., Armesto D, Org Lett. 2010 12 4082
76. Edmonds D J., Muir K W., Procter D J., J. Org. Chem. 2003 68 3190
77. Harb H Y., Collins K D., Altur J V. G., Bowker S, Campbell L, Procter D J., Org. Lett. 2010 12 5446
78. Fleming I, Henning R, Parker D C., Plaut H E., Sanderson P E. J., J. Chem. Soc., Perkin Trans. 1 1995 317
79. Wendeborn S, Binot G, Nina M, Winkler T, Synlett 2002 1683
80. Ager D J., Synthesis 1984 384
81. Pulici M, Sugawara F, Koshino H, Uzawa J, Yoshida S, Lobkovsky E, Clardy J, J. Org. Chem. 1996 61 2122
82. Rodríguez A, Nomen M, Spur B W., Godfroid J J., Tetrahedron Lett. 1999 40 5161
83. Takai K, Kimura K, Kuroda T, Hiyama T, Nozaki H, Tetrahedron Lett. 1983 24 5281
84. Jin H, Uenishi J J., Christ W J., Kishi Y, J. Am. Chem. Soc. 1986 108 5644
85. Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H, J. Am. Chem. Soc. 1986 108 6048
86. Baker T M., Edmonds D J., Hamilton D, OBrien C J., Procter D J., Angew. Chem. Int. Ed. 2008 47 5631
87. Pastor I M., Yus M, Curr. Org. Chem. 2007 11 925
88. Magnani R F., Rodrigues-Fo E, Daolio C, Ferreira A G., de Souza A Q. L., Z. Naturforsch., C: J. Biosci. 2003 58 319