Stereoselective synthesis of (+)-pericosine B and (+)-pericosine C using ring closing metathesis approach

Tetrahedron Asymmetry

Volumn 23, Issue 1, 2012, Pages 86-93

  Muniraju, Ch ^a   Rao, J Prasada ^a   Rao, B Venkateswara ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBASUGAR; PERICOSINE B; PERICOSINE C; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 84858297673     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.01.002     Document Type: Article

References (42)

1. O. Arjona, A.M. Gomez, J.C. Lopez, and J. Plumet Chem. Rev. 107 2007 1919
2. J. Plumet, A.M. Gomez, and J.C. Lopez Min. Rev. Org. Chem. 4 2007 201
3. G.E. McCasland, S. Furuta, and L.J. Durham J. Org. Chem. 31 1966 1516
4. T. Suami, and S. Ogawa Adv. Carbohydr. Chem. Biochem. 48 1990 21
5. N. Asano Glycobiology 13 2003 10
6. E.B. de Melo, A.S. Gomes, and I. Carvalho Tetrahedron 62 2006 10277
7. L. Cipolla, A. Araujo, D. Bini, L. Gabrielli, L. Russo, and N. Shaikh Expert. Opin. Drug Discov. 5 2010 721
8. L. Cipolla, B.L. Ferla, C. Airoldi, C. Zona, A. Orsato, N. Shaikh, L. Russo, and F. Nicotra Future Med. Chem. 2 2010 587
9. A. Numata, M. Iritani, T. Yamada, K. Minoura, E. Matsumura, T. Yamori, and T. Tsuruo Tetrahedron Lett. 38 1997 8215
10. T. Yamada, M. Iritani, H. Ohishi, K. Tanaka, M. Doi, K. Minoura, and A. Numata Org. Bioorg. Chem. 5 2007 3979
11. Review on Pericosines synthesis Y. Usami, H. Ichikawa, and M. Arimoto Int. J. Mol. Sci. 9 2008 401
12. Y. Usami, Y. Horibe, I. Takoaka, H. Ichikawa, and M. Arimoto Synlett 2006 1598
13. Y. Usami, Y. Horibe, I. Takoaka, H. Ichikawa, Y. Horibe, S. Tomiyama, M. Ohtsuka, Y. Imanishi, and M. Arimoto J. Org. Chem. 72 2007 6127
14. Y. Usami, K. Mizuki, H. Ichikawa, and M. Arimoto Tetrahedron: Asymmetry 2008 1461
15. Y. Usami, and K. Mizuki J. Nat. Prod. 74 2011 877
16. Y. Usami, M. Ohsugi, I. Takoaka, H. Ichikawa, and M. Arimoto Org. Lett. 11 2009 2699
17. T. Subhankar, S. Ajam Chand, and C. Chinpiao Org. Biomol. Chem. 9 2011 7306
18. S.Y. Reddy, P. Kadigachalam, K.R. Basak, and D.Y. Vankar Tetrahedron Lett. 53 2012 132
19. Y. Usami, and A. Numata Chem. Pharm. Bull. 52 2004 1125
20. T.J. Donohoe, K. Blades, M. Helliwell, and M.J. Waring Tetrahedron Lett. 39 1998 8755
21. J.L. Garcia, J.L. Cantarero, and C. Alemparte Phosphorus, Sulpur, Silicon 180 2005 1493
22. Y. Usami, C. Hatsuno, H. Yamamoto, M. Tanabe, and A. Numata Chem. Pharm. Bull. 52 2004 1130
23. R.D. Boyd, D.N. Sharma, A.C. Acaru, F.J. Malone, R.C. O'Dowd, C.R. Allen, and J.P. Stevenson Org. Lett. 12 2010 2206
24. Y. Usami, K. Suzuki, K. Mizuki, H. Ichikawa, and M. Arimoto Org. Biomol. Chem. 7 2009 315
25. Y. Usami, Y. Okada, and T. Yamada Chirality 23 2011 7
26. For an authoritative review of the area and a summary of the extensive studies at Roche, see: S. Albrecht, P. Harrington, H. Iding, M. Karpf, B. Wirz, and U. Zutter Chimia 58 2004 621
27. Y.-Y. Yeung, S. Hong, and E.J. Corey J. Am. Chem. Soc. 128 2006 6310
28. T.K.M. Shing, H.M. Cheng, W.F. Wong, C.S.K. Kwong, J. Li, C.B.S. Lau, P.S. Leung, and C.H.K. Cheng Org. Lett. 10 2008 3145
29. G.V. Ramana, and B.V. Rao Tetrahedron Lett. 46 2005 3049
30. J.P. Rao, and B.V. Rao Tetrahedron: Asymmetry 21 2010 930
31. G.P. Mishra, and B.V. Rao Tetrahedron Asymmetry 22 2011 812
32. H. Jin, J. Uenishi, W.J. Christ, and Y. Kishi J. Am. Chem. Soc. 108 1986 5644
33. K. Takai, M. Tagashira, K. Kuroda, K. Oshima, K. Utimoto, and H. Nozaki J. Am. Chem. Soc. 108 1986 6048
34. A. Furstner Chem. Rev 99 1999 991 and references cited therein
35. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
36. B.S. Bal, W.E. Childers, and H.W. Pinnick Tetrahedron 37 1981 2091
37. S. Guillarme, and A. Haudrechy Tetrahedron Lett. 46 2005 3175
38. S. Guillarme, K. Ple, A. Banchet, A. Liard, and A. Haudrechy Chem. Rev. 106 2006 2355 and references cited therein
39. M. Mori, N. Sakakibara, and A. Kinoshita J. Org. Chem. 63 1998 6082
40. P.R. Krishna, and M. Narsingam Tetrahedron Lett. 48 2007 8721
41. P.R. Krishna, and M. Alivelu Tetrahedron Lett. 51 2010 6265
42. O. Arjona, F. Iradier, R. Medel, and J. Plumet Tetrahedron: Asymmetry 10 1999 3431