Asymmetric synthesis of (+)-stagonolide C and (-)-aspinolide A via organocatalysis

Tetrahedron Asymmetry

Volumn 23, Issue 22-23, 2012, Pages 1534-1541

  Shelke, Anil M ^a   Rawat, Varun ^a   Suryavanshi, Gurunath ^a   Sudalai, Arumugam ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ASPINOLIDE A; LACTONE DERIVATIVE; PROLINE; STAGONOLIDE C; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; EPOXIDATION; ESTERIFICATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84870265984     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.10.007     Document Type: Article

References (30)

1. M. Tsuda, T. Mugishima, K. Komatsu, T. Sone, M. Tanaka, Y. Mikami, and J. Kobayashi J. Nat. Prod. 66 2003 412.
2. T.G. Back Tetrahedron 33 1977 3041.
3. C.J. Roxburgh Tetrahedron 49 1993 10749.
4. J. Fuchser, and A. Zeeck Liebigs Ann. Recl. 1997 87.
5. O. Yuzikhin, G. Mitina, and A. Berestetskiy J. Agric. Food Chem. 55 2007 7707.
6. A. Evidente, A. Cimmino, A. Berestetskiy, G. Mitina, A. Andolfi, and A. Motta J. Nat. Prod. 71 2008 31.
7. A. Evidente, A. Cimmino, A. Berestetskiy, A. Andolfi, and A. Motta J. Nat. Prod. 2008 1897 71.
8. H. Greve, P.J. Schupp, E. Eguereva, S. Kehraus, and G.M. Konig J. Nat. Prod. 71 2008 1651.
9. I. Shiina Chem. Rev. 107 2007 239.
10. D.K. Mohapatra, U. Dash, P.R. Naidu, and J.S. Yadav Synlett 2009 2129.
11. N. Jana, T. Mahapatra, and S. Nanda Tetrahedron: Asymmetry 20 2009 2622.
12. J.-Z. Wu, Z. Wang, and C. Qiao Tetrahedron Lett. 53 2012 1153.
13. J.S. Yadav, N.M. Reddy, N.V. Rao, M.A. Rahman, and A.R. Prasad Helv. Chim. Acta 95 2012 227.
14. P.S. Chowdhury, P. Gupta, and P. Kumar Tetrahedron Lett. 50 2009 7018.
15. G. Sabitha, T.R. Reddy, C. Srinivas, and J.S. Yadav Helv. Chim. Acta 94 2011 224.
16. For a review of proline-catalyzed asymmetric reactions, see: B. List Tetrahedron 58 2002 5573.
17. Y. Hayashi, J. Yamaguchi, K. Hibino, and M. Shoji Tetrahedron Lett. 44 2003 8293.
18. Y. Hayashi, J. Yamaguchi, T. Sumiya, and M. Shoji Angew. Chem., Int. Ed. 43 2004 1112.
19. S.P. Brown, M.P. Brochu, C.J. Sinz, and D.W.C. MacMillan J. Am. Chem. Soc. 125 2003 10808.
20. A. Cordova, H. Sunden, A. Bogevig, M. Johansson, and F. Himo Chem. Eur. J. 10 2004 3673.
21. G. Zhong, and Y. Yu Org. Lett. 6 2004 1637.
22. S.P. Kotkar, V.B. Chavan, and A. Sudalai Org. Lett. 9 2007 1001.
23. G.-L. Zhao, W.-W. Liao, and A. Cordova Tetrahedron Lett. 47 2006 4929.
24. I.K. Mangion, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 3696.
25. V. Rawat, P.V. Chouthaiwale, V.B. Chavan, G. Suryavanshi, and A. Sudalai Tetrahedron Lett. 51 2010 6565.
26. D. Devalankar, P.V. Chouthaiwale, and A. Sudalai Tetrahedron: Asymmetry 23 2012 240.
27. S. Kumar, V. Venkataramasubramaniyan, and A. Sudalai Org. Lett. 14 2012 2468.
28. H.C. Brown, and P.K. Jadhav J. Am. Chem. Soc. 105 1983 2092.
29. M.V.R. Reddy, A.J. Yucel, and P.V. Ramachandran J. Org. Chem. 66 2001 2512.
30. M. Marigo, J. Franzen, T.B. Poulsen, W. Zhuang, and K.A. Jorgensen J. Am. Chem. Soc. 127 2005 6964.