Total synthesis of (+)-pericosine B and (+)-pericosine C and their enantiomers by using the Baylis-Hillman reaction and ring-closing metathesis as key steps

Tetrahedron Letters

Volumn 53, Issue 2, 2012, Pages 132-136

  Reddy, Y Suman ^a   Kadigachalam, P ^a   Basak, Ranjan K ^a   John Pal, A P ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Baylis Hillman reaction; Carbasugars; Hoveyda Grubbs catalyst; Pericosine; Ring closing metathesis

Indexed keywords

ANTINEOPLASTIC AGENT; PERICOSINE A; PERICOSINE B; PERICOSINE C; PERICOSINE D; PERICOSINE E; RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG SYNTHESIS; ENANTIOMER; RING CLOSING METATHESIS;

EID: 83555176295     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.135     Document Type: Article

References (51)

1. Y. Usami, and K. Mizuki J. Nat. Prod. 74 2011 877 881
2. T. Yamada, M. Iritani, H. Ohishi, K. Tanaka, M. Doi, K. Minoura, and A. Numata Org. Biomol. Chem. 5 2007 3979 3986
3. A. Numata, M. Iritani, T. Yamada, K. Minoura, E. Matsumura, T. Yamori, and T. Tsuruo Tetrahedron Lett. 38 1997 8215 8218
4. Y. Usami, H. Ichikawa, and M. Arimoto Int. J. Mol. Sci. 9 2008 401 421
5. G. Mehta, and S. Sen Tetrahedron Lett. 51 2010 503 507
6. G. Mehta, S. Roy, and R.A. Davis Tetrahedron Lett. 49 2008 5162 5164
7. O. Arjona, A.M. Gomez, J.C. Lopez, and J. Plumet Chem. Rev. 107 2007 1919 2036
8. R. Alibes, P. Bayon, P. March, M. Figueredo, J. Font, and G. Marjanet Org. Lett. 8 2006 1617 1620
9. L. Sanchez-Abella, S. Fernandez, N. Armesto, M. Ferrero, and V. Gotor J. Org. Chem. 71 2006 5396 5399
10. D.J. Newman, and G.M. Cragg Curr. Drug Targets 7 2006 279 304
11. W. Fenical, and P.R. Jensen Nat. Chem. Biol. 2 2006 666 673
12. For reviews, see: T. Suami Pure Appl. Chem. 59 1987 1509 1520
13. T. Suami, and S. Ogawa Adv. Carbohydr. Chem. Biochem. 48 1990 21 90
14. T. Suami Top. Curr. Chem. 154 1990 257 283
15. A. Berecibar, C. Grandjean, and A. Siriwardena Chem. Rev. 99 1999 779 844
16. Y. Usami, K. Suzuki, K. Mizuki, H. Ichikawa, and M. Arimoto Org. Biomol. Chem. 7 2009 315 318
17. Y. Usami, M. Ohsugi, K. Mizuki, H. Ichikawa, and M. Arimoto Org. Lett. 11 2009 2699 2701
18. Y. Usami, K. Mizuki, H. Ichikawa, and M. Arimoto Tetrahedron: Asymmetry 19 2008 1461 1464
19. Y. Usami, I. Takaoka, H. Ichikawa, Y. Horibe, S. Tomiyama, M. Ohtsuka, Y. Imanishi, and M. Arimoto J. Org. Chem. 72 2007 6127 6134
20. Y. Usami, and Y. Ueda Synthesis 2007 3219 3225
21. Y. Usami, Y. Horibe, I. Takaoka, H. Ichikawa, and M. Arimoto Synlett 2006 1598 1600
22. Y. Usami, and Y. Ueda Chem. Lett. 34 2005 1062 1063
23. Y. Usami, C. Hatsuno, H. Yamamoto, M. Tanabe, and A. Numata Chem. Pharm. Bull. 52 2005 1130 1133
24. Z. Fejes, A. Mándi, I. Komáromi, A. Bényei, L. Naesens, F. Fenyvesi, L. Szilágyi, and P. Herczegh Tetrahedron 65 2009 8171 8175
25. D.R. Boyd, N.D. Sharma, C.A. Acaru, J.F. Malone, C.R. O'Dowd, C.C.R. Allen, and P.J. Stevenson Org. Lett. 12 2010 2206 2209
26. T.J. Donohoe, K. Blades, M. Helliwell, M.J. Waring, and N.J. Newcombe Tetrahedron Lett. 39 1998 8755 8758
27. V.R. Doddi, and Y.D. Vankar Eur. J. Org. Chem. 2007 5583 5589
28. P.R. Krishna, and R.R. Kadiyala Tetrahedron Lett. 51 2010 2586 2588
29. Y.S. Reddy, A.P. John Pal, P. Gupta, A.A. Ansari, and Y.D. Vankar J. Org. Chem. 76 2011 5972 5984
30. P.K. Kancharla, Y.S. Reddy, S. Dharuman, and Y.D. Vankar J. Org. Chem. 76 2011 5832 5837
31. A.P. John Pal, and Y.D. Vankar Tetrahedron Lett. 51 2010 2519 2524
32. P.K. Kancharla, and Y.D. Vankar J. Org. Chem. 75 2010 8457 8464
33. G.K. Rawal, S. Rani, N. Kumari, and Y.D. Vankar J. Org. Chem. 74 2009 5349 5355
34. G.K. Rawal, A. Kumar, U. Tawar, and Y.D. Vankar Org. Lett. 9 2007 5171 5174
35. B.G. Reddy, K.P. Madhusudanan, and Y.D. Vankar J. Org. Chem. 69 2004 2630 2633
36. A. Kumar, G.K. Rawal, and Y.D. Vankar Tetrahedron 64 2008 2379 2390
37. K. Jayakanthan, and Y.D. Vankar Tetrahedron Lett. 47 2006 8667 8671
38. B.G. Reddy, and Y.D. Vankar Angew. Chem., Int. Ed. 44 2005 2001 2004 and references cited therein
39. P. Gupta, A.P. John Pal, Y.S. Reddy, and Y.D. Vankar Eur. J. Org. Chem. 2011 1166 1175
40. Y.S. Reddy, P. Kadigachalam, V.R. Doddi, and Y.D. Vankar Tetrahedron Lett. 50 2009 5827 5830
41. P.K. Kancharla, V.R. Doddi, H. Kokatla, and Y.D. Vankar Tetrahedron Lett. 50 2009 6951 6954
42. V.R. Doddi, A. Kumar, and Y.D. Vankar Tetrahedron 64 2008 9117 9122
43. K. Jayakanthan, and Y.D. Vankar Org. Lett. 7 2005 5441 5444
44. A.P. John Pal, P. Gupta, Y.S. Reddy, and Y.D. Vankar Eur. J. Org. Chem. 2010 6957 6966
45. N. Kumari, B.G. Reddy, and Y.D. Vankar Eur. J. Org. Chem. 2008 160 169
46. W.H. Kim, J.A. Kang, H.R. Lee, A.Y. Park, P. Chun, B. Lee, J. Kim, J.A. Kim, L.S. Jeong, and H.R. Moon Carbohydr. Res. 344 2009 2317 2321 and references therein
47. A.E. Greene, C.L. Drian, and P. Crabbe J. Am. Chem. Soc. 102 1980 7583 7584
48. D.B. Werz, and P.H. Seeberger Angew. Chem., Int. Ed. 44 2005 6315 6318
49. K.P. Kaliappan, V. Ravikumar, and A. Pujari J. Chem. Sci. 120 2008 205 216
50. G.V. Ramana, and B.V. Rao Tetrahedron Lett. 46 2005 3049 3051
51. S. Tripathi, A.C. Shaikh, and C. Chen Org. Biomol. Chem. 9 2011 7306 7308