Consecutive reactions with sulfoximines: Straightforward synthesis of substituted 5,5-spiroketals

Synthesis

Volumn , Issue 13, 2011, Pages 2085-2090

  Sridharan, Vellaisamy ^a   Vologdin, Nikolay ^a   Virolleaud, Marie Alice ^a   Bonne, Damien ^a   Bressy, Cyril ^a   Chouraqui, Gaëlle ^a   Commeiras, Laurent ^a   Parrain, Jean Luc ^a   Coquerel, Yoann ^a   Rodriguez, Jean ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

5,5 spiroketals; chalcogran; consecutive reaction; sulfoximine

Indexed keywords

SPEECH SYNTHESIS;

5,5-SPIROKETALS; CHALCOGRAN; CONSECUTIVE REACTION; DIRECT SYNTHESIS; EFFICIENT SYNTHESIS; EPOXIDE OPENINGS; SULFOXIMINES; TETRAHYDROFURANS;

CHEMISTRY;

5,5 SPIROKETAL DERIVATIVE; CHALCOGRAN; CHEMICAL COMPOUND; PHEROMONE DERIVATIVE; SULFOXIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL SPIROKETALIZATION; SUBSTITUTION REACTION;

EID: 79959373526     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260039     Document Type: Article

References (97)

1. For reviews on spiroketals, see:, Kluge A F., Heterocycles 1986 24 1699
2. Boivin T L. B., Tetrahedron 1987 43 3309
3. Perron F, Albizati K F., Chem. Rev. 1989 89 1617
4. Jacobs M F., Kitching W B., Curr. Org. Chem. 1998 2 395
5. Francke W, Kitching W, Curr. Org. Chem. 2001 5 233
6. Mead K T., Brewer B N., Curr. Org. Chem. 2003 7 227
7. Aho J E., Pihko P M., Rissa T K., Chem. Rev. 2005 105 4406
8. Raju B R., Saikia A K., Molecules 2008 13 1942
9. Favre S, Vogel P, Gerber-Lemaire S, Molecules 2008 13 2570
10. Hauske J R., Kostek G, J. Org. Chem. 1989 54 3500
11. Bell W, Block M H., Cook C, Grant J A., Timms D, J. Chem. Soc., Perkin Trans. 1 1997 2789
12. Brasholz M, Sörgel S, Azap C, Reißig H.-U, Eur. J. Org. Chem. 2007 3801
13. Ono M, Mishima H, Takiguchi Y, Terao M, J. Antibiot. 1983 36 509
14. Niggemann J, Bedorf N, Flörke U, Steinmetz H, Gerth K, Reichenbach H, Höfle G, Eur. J. Org. Chem. 2005 5013
15. Holtzel A, Kempter C, Metzger J W., Jung G, Groth I, Fritz T, Fiedler H.-P, J. Antibiot. 1998 51 699
16. Jia Y, Li X, Wang P, Wu B, Zhao X, Tu Y, [nl]J. Chem. Soc., Perkin Trans. 1 2002 565
17. Wang L, Floreancig P E., Org. Lett. 2004 6 569
18. Milroy L.-G, Zinzalla G, Loiseau F, Qian Z, Prencipe G, Pepper C, Fegan C, Ley S V., ChemMedChem 2008 3 1922
19. Wagner C E., Wang Q, Melamed A, Fairchild C R., Wild R, Heathcock C H., Tetrahedron 2007 64 124
20. Casu L, Bonsignore L, Pinna M, Casu M, Floris C, Gertsch J, Cottiglia F, [nl]J. Nat. Prod. 2006 69 295
21. Smith A B., Corbett R M., Pettit G R., Chapuis J.-C, Schmidt J M., Hamel E, Jung M K., Bioorg. Med. Chem. Lett. 2002 12 2039
22. Barun O, Kumar K, Sommer S, Langerak A, Mayer T U., Müller O, Waldmann H, Eur. J. Org. Chem. 2005 4773
23. Crimmins M T., Smith A C., Org. Lett. 2006 8 1003
24. Yunt Z, Reinhardt K, Li A, Engeser M, Dahse [nl]H.-M, Gütschow M, Bruhn T, Bringmann G, Piel J, [nl] J. Am. Chem. Soc. 2009 131 2297
25. Zhao X Z., Peng L, Tang M, Tu Y Q., Gao S H., Tetrahedron Lett. 2005 46 6941
26. For selected examples, see:, Hirai K, Ooi H, Esumi T, Iwabuchi Y, Hatakeyama S, Org. Lett. 2003 5 857
27. Tursun A, Canet I, Aboab B, Sinibaldi M.-E, Tetrahedron Lett. 2005 46 2291
28. deGreef M, Zard S Z., Org. Lett. 2007 9 1773
29. Ardes-Guisot N, Oulet-Lahoucine B, Canet I, Sinibaldi M.-E, Tetrahedron Lett. 2007 48 8511
30. Castagnolo D, Breuer I, Pikho P M., J. Org. Chem. 2007 72 10081
31. Sommer S, Kühn M, Waldmann H, Adv. Synth. Catal. 2008 350 1736
32. Tursun A, Aboab B, Martin A.-S, Sinibaldi M.-E, Canet I, Synlett 2005 2397
33. Dias L C., deOliveira L G., Org. Lett. 2004 6 2587
34. Crimmins M T., Rafferty S W., Tetrahedron Lett. 1996 37 5649
35. Enders D, Dahmen W, Dederichs E, Gatzweiler W, Weuster P, Synthesis 1990 1013
36. For selected examples, see:, Aponick A, Li C.-Y, Palmes J A., Org. Lett. 2009 11 121
37. Liu B, deBrabander J K., Org. Lett. 2006 8 4907
38. Zhang Y, Xue J, Xin Z, Xie Z, Li Y, Synlett 2008 940
39. Sherry B D., Maus L, Laforteza B N., Toste F D., [nl]J. Am. Chem. Soc. 2006 128 8132
40. Fujioka H, Nakahara K, Hirose H, Hirano K, Oki T, Kita Y, Chem. Commun. 2011 1060
41. Rizzacasa M A., Pollex A, Org. Biomol. Chem. 2009 7 1053; and references cited therein
42. Step economy
43. Wender P A., Verma V A., Paxton T J., Pillow T H., Acc. Chem. Res. 2008 41 40; and references cited therein
44. (b), Trost B M., Acc. Chem. Res. 2002 35 695, and references cited therein
45. (c), Burns N Z., Baran P S., Hoffmann R W., Angew. Chem. Int. Ed. 2009 48 2854
46. For a discussion, using cases-study from complex-molecule total syntheses, see:, Newhouse T, Baran P S., Hoffmann R W., Chem. Soc. Rev. 2009 38 3010
47. For a discussion on terminologies, see:, Coquerel Y, Boddaert T, Presset M, Mailhol D, Rodriguez J, In Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry Pignataro B Wiley-VCH Weinheim 2010 Chap. 9 187-202; and references cited therein
48. Sheldon R A., Arends I, Hanefeld U, Green Chemistry and Catalysis Wiley-VCH Weinheim 2007 and references cited therein
49. For selected recent examples, see:, Coquerel Y, Filippini M.-H, Bensa D, Rodriguez J, Chem. Eur. J. 2008 14 3078
50. Bonne D, Salat L, Dulcère J.-P, Rodriguez J, Org. Lett. 2008 10 5409
51. Liéby-Müller F, Allais C, Constantieux T, Rodriguez J, Chem. Commun. 2008 4207
52. Allais C, Constantieux T, Rodriguez J, Chem. Eur. J. 2009 15 12945
53. Dumez E, Durand A.-C, Guillaume M, Roger P.-Y, Faure R, Pons J.-M, Herbette G, Dulcère J.-P, Bonne D, Rodriguez J, Chem. Eur. J. 2009 15 12470
54. Boddaert T, Coquerel Y, Rodriguez J, Adv. Synth. Catal. 2009 351 1744; Corrigendum: Adv. Synth. Catal. 2009, 351, 2541
55. Presset M, Coquerel Y, Rodriguez J, Org. Lett. 2009 11 5706
56. Raimondi W, Lettieri G, Dulcère J.-P, Bonne D, Rodriguez J, Chem. Commun. 2010 46 7247
57. Presset M, Coquerel Y, Rodriguez J, Org. Lett. 2010 12 4212
58. Boddaert T, Coquerel Y, Rodriguez J, Chem. Eur. J. 2011 17 2048
59. Coquerel Y, Rodriguez J, Tetrahedron Lett. 2006 47 8503
60. Virolleaud M.-A, Sridharan V, Mailhol D, Bonne D, Bressy C, Chouraqui G, Commeiras L, Coquerel Y, Rodriguez J, Tetrahedron 2009 65 9756
61. Johnson C R., Aldrichimica Acta 1985 18 3
62. Reggelin M, Zur C, Synthesis 2000 1
63. Okamura H, Bolm C, Chem. Lett. 2004 33 482
64. Worch C, Mayer A C., Bolm C, In Organosulfur Chemistry in Asymmetric Synthesis Toru T Bolm C Wiley-VCH Weinheim 2008 209-229
65. Gais H.-J, Heteroat. Chem. 2007 18 472
66. For epoxide opening with -lithiated alkenylsulfones, see
67. McCombie S W., Shankar B B., Ganguly A K., Tetrahedron Lett. 1985 26 6301
68. McCombie S W., Shankar B B., Ganguly A K., Tetrahedron Lett. 1987 28 4127
69. Yamamoto M, Takemori T, Iwasa S, Kohmoto S, Yamada K, J. Org. Chem. 1989 54 1757
70. Padwa A, Bullock W H., Dyszlewski A D., McCombie S W., Shankar B B., Ganguly A K., J. Org. Chem. 1991 56 3556
71. Jung M E., Toyota A, Tetrahedron Lett. 2000 41 3577
72. Auvray P, Knochel P, Normant J.-F, Tetrahedron Lett. 1986 27 5091
73. Iwata C, Fujita M, Moritani Y, Hattori K, Imanishi T, Tetrahedron Lett. 1987 28 3135
74. Craig D, Ikin N J., Mathews N, Smith A M., Tetrahedron 1999 55 13471
75. Sklute G, Marek I, [nl]J. Am. Chem. Soc. 2006 128 4642
76. For previous use of -lithiated alkenylsulfoximines in synthesis, see:, Gais H.-J, Müller H, Decker J, Hainz R, Tetrahedron Lett. 1995 36 7433
77. Reddy L R., Gais H.-J, Woo C.-W, Raabe G, J. Am. Chem. Soc. 2002 124 10427
78. Gais H.-J, Loo R, Roder D, Das P, Raabe G, Eur. J. Org. Chem. 2003 1500
79. Lejkowki M, Gais H.-J, Banerjee P, Vermeeren C, J. Am. Chem. Soc. 2006 128 15378
80. Lejkowki M, Banerjee P, Runsink J, Gais H.-J, Org. Lett. 2008 10 2713
81. Gais H.-J, Rao C V., Loo R, Chem. Eur. J. 2008 14 6510
82. Chemla F, Vranken E, In The Chemistry of Organolithium Compounds Rappoport Z Marek I Wiley New York 2004 1165-1242
83. Taber D F., Joerger J.-M, J. Org. Chem. 2007 72 3454
84. Betancor C, Freire R, Pérez-Martín I, Prangé T, Suárez E, Org. Lett. 2002 4 1295
85. Lee J S., Fuchs P L., Org. Lett. 2003 5 2247
86. Tlais S F., Dudley G B., Org. Lett. 2010 12 4698
87. Awasaguchi K.-i, Miyazawa M, Uoya I, Inoue K, Nakamura K, Yokoyama H, Kakuda H, Hirai Y, Synlett 2010 2392
88. Doubsky J, Streinz L, aman D, Zedník J, Koutek B, Org. Lett. 2004 6 4909
89. Tiecco M, Testaferri L, Bagnoli L, Scarponi C, Temperini A, Marini F, Santi C, Tetrahedron: Asymmetry 2006 17 2768
90. DosSantos A A., Princival J L., Comasseto J V., deBarros S M. G., BrainerNeto J E., Tetrahedron 2007 63 5167
91. Tony K A., Li X, Dabideen D, Li J, Mootoo D R., Org. Biomol. Chem. 2008 6 1165
92. Selvaratnam S, Ho J H. H., Huleatt P B., Messerle B A., Chai C L. L., Tetrahedron Lett. 2009 50 1125
93. Isolation
94. Francke W, Heemann V, Gerken B, Renwick J A. A., Vité J P., Naturwissenschaften 1977 64 590
95. Trapp O, Schurig V, Chem. Eur. J. 2001 7 1495; and references 10-12 cited therein
96. Cubero I I., Lopez-Espinosa M T. P., Kari N, Carbohydr. Res. 1994 261 231
97. Hungerbühler E, Naef R, Wasmuth D, Seebach D, Loosli H.-R, Wehrli A, Helv. Chim. Acta 1980 63 1960