A common approach to the total synthesis of l-arabino-, l-ribo-C 18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose

Tetrahedron

Volumn 69, Issue 38, 2013, Pages 8228-8244

  Martinková, Miroslava ^a   Pomikalová, Kvetoslava ^a   Gonda, Jozef ^a   Vilková, Mária ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

Isothiocyanates; Jaspine B; Phytosphingosine; Rearrangements; Sphingolipids; Trichloroacetamides

Indexed keywords

3 EPI JASPINE B; CHLORIDE; ENT 2 EPI JASPINE B; L ARABINO PHYTOSPHINGOSINE; L RIBO C18 PHYTOSPHINGOSINE; MANNOSE; PHYTOSPHINGOSINE; THIOCYANATE; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 84881169441     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.07.028     Document Type: Article

References (84)

1. T. Kolter, and K. Sandhoff Angew. Chem., Int. Ed. 38 1999 1532 1568
2. Y.D. Vankar, and R.R. Schmidt Chem. Soc. Rev. 29 2000 201 206
3. A.H. Merrill Jr., and K. Sandhoff D.E. Vance, J.E. Vance, Biochemistry of Lipids, Lipoproteins, and Membranes 4th ed. 2002 Elsevier Amsterdam 373 407
4. J. Liao, J. Tao, G. Lin, and D. Liu Tetrahedron 61 2005 4715 4733
5. T. Wennekes, R.J.B.H.N. van den Berg, R.G. Boot, G.A. van der Marel, H.S. Overkleeft, and J.M.F.G. Aerts Angew. Chem., Int. Ed. 48 2009 8848 8868
6. D. Enders, V. Terteryan, and J. Paleček Synthesis 2010 2979 2984 and references cited therein
7. M. Schombs, F.E. Park, W. Du, S.S. Kulkarni, and J. Gervay-Hague J. Org. Chem. 75 2010 4891 4898
8. S.D. Khaja, V. Kumar, M. Ahmad, J. Xue, and K.L. Matta Tetrahedron Lett. 51 2010 4411 4414
9. Z. Liu, H.-S. Byun, and R. Bittman Org. Lett. 12 2010 2974 2977
10. B. Roy, S. Ferdjani, C. Tellier, and C. Rabiller Tetrahedron 67 2011 5176 5183
11. P.J. Jervis, L.R. Cox, and G.S. Besra J. Org. Chem. 76 2011 320 323
12. X. Zhu, R.T. Dere, and J. Jiang Tetrahedron Lett. 52 2011 4971 4974
13. N. Veerapen, F. Reddington, M. Salio, V. Cerundolo, and G.S. Besra Bioorg. Med. Chem. 19 2011 221 228
14. Z. Liu, and R. Bittman Org. Lett. 14 2012 620 623
15. T. Tashiro, T. Shigeura, H. Watarai, M. Taniguchi, and K. Mori Bioorg. Med. Chem. 20 2012 4540 4548
16. M. Shiozaki, T. Tashiro, H. Koshino, T. Shigeura, H. Watarai, M. Taniguchi, and K. Mori Carbohydr. Res. 370 2013 46 66
17. P.M. Koskinen, and A.M.P. Koskinen Synthesis 1998 1075 1091
18. A.R. Howell, and A.J. Ndakala Curr. Org. Chem. 6 2002 365 391
19. A.R. Howell, R.C. So, and S.K. Richardson Tetrahedron 60 2004 11327 11347
20. J.A. Morales-Serna, J. Llaveria, Y. Díaz, M.I. Matheu, and S. Castillón Curr. Org. Chem. 14 2010 2483 2521
21. I. Kuroda, M. Musman, I. Ohtani, T. Ichiba, J. Tanaka, D. Garcia-Gravalos, and T. Higa J. Nat. Prod. 65 2002 1505 1506
22. V. Ledroit, C. Debitus, C. Lavaud, and G. Massoit Tetrahedron Lett. 44 2003 225 228
23. D. Canals, D. Mormeneo, G. Fabriàs, A. Llebaria, J. Casas, and A. Delgado Bioorg. Med. Chem. 17 2009 235 241
24. Y. Yoshimitsu, S. Oishi, J. Miyagaki, S. Inuki, H. Ohno, and N. Fujii Bioorg. Med. Chem. 19 2011 5402 5408
25. G. Pandey, and D.K. Tiwari Tetrahedron Lett. 50 2009 3296 3298
26. A. Dubey, and P. Kumar Tetrahedron Lett. 50 2009 3425 3427
27. P. Kumar, A. Dubey, and V.G. Puranik Org. Biomol. Chem. 8 2010 5074 5086
28. Z. Liu, H.-S. Byun, and R. Bittman J. Org. Chem. 75 2010 4356 4364
29. Y.M. Lee, D.J. Beak, S. Lee, D. Kim, and S. Kim J. Org. Chem. 76 2011 408 416
30. M. Martinková, J. Gonda, K. Pomikalová, J. Kožíšek, and J. Kuchár Carbohydr. Res. 346 2011 1728 1738
31. G.S. Rao, and B.V. Rao Tetrahedron Lett. 52 2011 4861 4864
32. Y.M. Lee, S. Lee, H. Jeon, D.J. Beak, J.H. Seo, D. Kim, and S. Kim Synthesis 2011 867 872
33. R.S. Perali, S. Mandava, and S. Chalapala Tetrahedron 67 2011 9283 9290
34. G.S. Rao, and B.V. Rao Tetrahedron Lett. 52 2011 6076 6079
35. Y. Mu, T. Jin, G.-W. Kim, J.-S. Kim, S.-S. Kim, Y.-S. Tian, C.-Y. Oh, and W.-H. Ham Eur. J. Org. Chem. 2012 2614 2620
36. G.S. Rao, B. Chandrasekhar, and B.V. Rao Tetrahedron: Asymmetry 23 2012 564 569
37. Y. Mu, J.-Y. Kim, X. Jin, S.-H. Park, J.-E. Joo, and W.-H. Ham Synthesis 44 2012 2340 2346
38. C. Xarnod, W. Huang, R.-G. Ren, R.-C. Liu, and B.-G. Wei Tetrahedron 68 2012 6688 6695
39. A.J. Cresswell, S.G. Davies, J.A. Lee, M.J. Morris, P.M. Roberts, and J.E. Thomson J. Org. Chem. 77 2012 7262 7281
40. R. Mettu, N.R. Thatikonda, O.S. Olusegun, R. Vishvakarma, and J.R. Vaidya ARKIVOC 2012 421 436
41. M. Martinková, K. Pomikalová, and J. Gonda Chem. Pap. 67 2013 84 91
42. Y.-F. Yen, R.C. Sawant, and S.-Y. Luo Synthesis 45 2013 511 517
43. T.J. Devi, B. Saikia, and N.C. Barua Tetrahedron 69 2013 3817 3822
44. For a review on isolation, chemistry and syntheses of jaspine B and its 2-epi-anolog, see: E. Abraham, S.G. Davies, P.M. Roberts, A.J. Russell, and J.E. Thomson Tetrahedron: Asymmetry 19 2008 1027 1047
45. D. Enders, V. Terteryan, and J. Paleček Synthesis 2008 2278 2282
46. Y. Ichikawa, K. Matsunaga, T. Masuda, H. Kotsuki, and K. Nakano Tetrahedron 64 2008 11313 11318
47. G. Reddipalli, M. Venkataiah, M.K. Mishra, and N.W. Fadnavis Tetrahedron: Asymmetry 20 2009 1802 1805
48. Y. Yoshimitsu, S. Inuki, S. Oishi, N. Fujii, and H. Ohno J. Org. Chem. 75 2010 3843 3846
49. G.S. Rao, N. Sudhakar, B.V. Rao, and S.J. Basha Tetrahedron: Asymmetry 21 2010 1963 1970
50. P. Vichare, and A. Chattopadhyay Tetrahedron: Asymmetry 21 2010 1983 1987
51. G. Jayachitra, N. Sudhakar, R.K. Anchoori, B.V. Rao, S. Roy, and R. Banerjee Synthesis 2010 115 119
52. Y. Salma, S. Ballereau, C. Maaliki, S. Ladeira, N. Andrie-Abadie, and Y. Génisson Org. Biomol. Chem. 8 2010 3227 3243
53. J. Llaveria, Y. Díaz, M.I. Matheu, and S. Castillón Eur. J. Org. Chem. 2011 1514 1519
54. K.R. Prasad, and K. Penchalaiah Tetrahedron: Asymmetry 22 2011 1400 1403
55. S. Cruz-Gregorio, C. Espinoza-Rojas, L. Quinter, and F. Sartillo-Piscil Tetrahedron Lett. 52 2011 6370 6371
56. A. Sánchez-Eleuterio, L. Quintero, and F. Sartillo-Piscil J. Org. Chem. 76 2011 5466 5471
57. H. Bae, H. Jeon, D.J. Beak, D. Lee, and S. Kim Synthesis 44 2012 3609 3612
58. D. Lee Synlett 2012 2840 2844
59. M.-L. Zhao, E. Zhang, J. Gao, Z. Zhang, Y.-T. Zhao, W. Qu, and H.-M. Lui Carbohydr. Res. 351 2012 126 129
60. Y. Yoshimitsu, J. Miyagaki, S. Oishi, N. Fujii, and H. Ohno Tetrahedron 69 2013 4211 4220
61. S. Baskaran, M.H.A. Baig, S. Banerjee, C. Baskaran, K. Bhanu, S.P. Deshpande, and G.K. Trivedi Tetrahedron 52 1996 6437 6452
62. P.P. Singh, M.M. Gharia, F. Dasgupta, and H.C. Srivastava Tetrahedron Lett. 5 1977 439 440
63. P.M. Collins, W.G. Overend, and T. Shing J. Chem. Soc., Chem. Commun. 1981 1139 1140
64. L.E. Overman, and N.E. Carpenter L.E. Overman, Organic Reactions Vol. 66 2005 Wiley New York, NY 1 107 and references cited therein
65. T. Nishikawa, M. Asai, N. Ohyabu, and M. Isobe J. Org. Chem. 63 1998 188 192
66. J. Gonda, M. Martinková, A. Zadrošová, M. Šoteková, J. Raschmanová, P. Čonka, E. Gajdošíková, and C.O. Kappe Tetrahedron Lett. 48 2007 6912 6915
67. E. Gajdošíková, M. Martinková, J. Gonda, and P. Čonka Molecules 13 2008 2837 2847
68. M. Martinková, J. Gonda, A. Uhríková, J. Špaková Raschmanová, and J. Kuchár Carbohydr. Res. 352 2012 23 36
69. L.E. Overman J. Am. Chem. Soc. 96 1974 597 599
70. L.E. Overman J. Am. Chem. Soc. 98 1976 2901 2910
71. J. Gonda, A.-C. Helland, B. Ernst, and D. Belluš Synthesis 1993 729 734
72. C.E. Andersom, and L.E. Overman J. Am. Chem. Soc. 125 2003 12412 12413
73. I. Jaunzeme, and A. Jirgensons Synlett 2005 2984 2986
74. I. Jaunzeme, and A. Jirgensons Tetrahedron 64 2008 5794 5799
75. A. Sutherland, and M.D. Swift Tetrahedron 64 2008 9521 9527
76. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian Wallingford CT
77. N. Òelebi-ÖlÒüm, V. Aviyente, and K.N. Houk J. Org. Chem. 74 2009 6944 6952
78. L. Kniežo, J. Bernát, and M. Martinková Chem. Pap. 48 1994 103 107
79. L. Battistini, C. Curti, F. Zanardi, G. Rassu, L. Auzzas, and G. Casiraghi J. Org. Chem. 69 2004 2611 2613
80. H. Azuma, S. Tamagaki, and K. Ogino J. Org. Chem. 65 2000 3538 3541
81. R.J.B.H.N. van den Berg, T.J. Boltje, C.P. Verhagen, R.E.J.N. Litjens, G.A. van der Marel, and H.S. Overkleeft J. Org. Chem. 71 2006 836 839
82. E. Abraham, E.A. Brock, J.I. Candela-Lena, S.G. Davies, M. Georgiou, R.L. Nicholson, J.H. Perkins, P.M. Roberts, A.J. Russell, E.M. Sánchez- Fernández, P.M. Scott, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 6 2008 1665 1673
83. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112 122
84. A.L. Spek J. Appl. Crystallogr. 36 2003 7 13