Total synthesis of palmyrolide A and its 5,7-epi isomers

Tetrahedron

Volumn 69, Issue 11, 2013, Pages 2419-2429

  Sudhakar, Gangarajula ^a   Reddy, Karla Janardhan ^a   Nanubolu, Jagadeesh Babu ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Macrocyclization; N Methyl enamide; Natural products; Neuroactive macrolide; Total synthesis

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; MACROLIDE; PALMYROLIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ESTERIFICATION; HYDROGENATION; ISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 84873734100     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.048     Document Type: Article

References (28)

1. S. Matthew, L.A. Salvador, P.J. Schupp, V.J. Paul, and H. Luesch J. Nat. Prod. 73 2010 1544 1552
2. D. Klen, J.C. Braekman, D. Daloze, L. Hoffmann, G. Castillo, and V. Demoulin J. Nat. Prod. 62 1999 934 936
3. D. Klein, J.C. Braekman, and D. Daloze Tetrahedron Lett. 37 1996 7519 7520
4. A.R. Pereira, Z. Cao, N. Engene, I.E.S. Mercado, T.F. Murray, and W.H. Gerwick Org. Lett. 12 2010 4490 4493
5. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, and K. Tachibana J. Org. Chem. 64 1999 866 876
6. R. Tello-Aburto, E.M. Johnson, C.K. Valdez, and W.A. Maio Org. Lett. 14 2012 2150 2153
7. R. Tello-Aburto, T.D. Newar, and W.A. Maio J. Org. Chem. 77 2012 6271 6289
8. A.D. Wadsworth, D.P. Furkert, J. Sperry, and M.A. Brimble Org. Lett. 14 2012 5374 5377
9. F. Richter, M. Bauer, C. Perez, C.M. Mssmer, and M.E. Maier J. Org. Chem. 67 2002 2474 2480
10. H. Nagano, and S. Hara Tetrahedron Lett. 45 2004 4329 4332
11. G. Sudhakar, K. Satish, and J. Raghavaiah J. Org. Chem. 77 2012 10010 10020
12. J.W.J. Kennedy, and D.G. Hall J. Org. Chem. 69 2004 4412 4428
13. R. Dumeunier, and I.E. Markó Tetrahedron Lett. 41 2000 10219 10222
14. L. Huang, Q. Wang, X. Liu, and H. Jiang Angew. Chem., Int. Ed. 51 2012 5696 5700
15. T. Suzuki, J. Atsumi, T. Sengoku, M. Takahashi, and H. Yoda J. Organomet. Chem. 695 2010 128 136
16. V. Rauniyar, and D.G. Hall J. Org. Chem. 74 2009 4236 4241
17. I. Chataigner, F. Zammattio, J. Lebreton, and J. Viilliéras Tetrahedron 64 2008 2441 2455
18. W. Adam, P. Groer, and C.R.S. Möller Tetrahedron: Asymmetry 11 2000 2239 2243
19. Y. Komatsu, F. Sasaki, S. Takei, and T. Kitazume J. Org. Chem. 63 1998 8058 8062
20. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguchi Bull. Chem. Soc. Jpn. 52 1979 1989 1993
21. C. Rabong, U. Jordis, and J.B. Phopase J. Org. Chem. 75 2010 2492 2500
22. K.C. Nicolaou, X. Jiang, P.J.L. Scott, A. Corbu, S. Yamashiro, A. Bacconi, and V.M. Fowler Angew. Chem., Int. Ed. 50 2011 1139 1144
23. J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron 51 1995 10801 10810
24. CCDC 905005 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html.
25. N.T. Patil, J.N. Tilekar, and D.D. Dhavale J. Org. Chem. 66 2001 1065 1074
26. A. Müller, C. Vogt, and N. Sewald Synthesis 1998 837 841
27. Z. Elkhayat, I. Safir, I. Castellote, P. Retailleau, and S. Arseniyadis Org. Lett. 10 2008 2219 2222
28. J.Y. Ma, W. Huang, and B.G. Wei Tetrahedron Lett. 52 2011 4598 4601