Total synthesis of bioactive drimane-epoxyquinol hybrid natural products: Macrophorin A, 4′-oxomacrophorin A, and 1′-epi-craterellin A

Tetrahedron Letters

Volumn 55, Issue 45, 2014, Pages 6252-6256

  Garai, Sumanta ^a   Mehta, Goverdhan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Drimanes; Epoxyquinols retroDiels Alder reaction; Hybrid natural products; Stereoselective reduction

Indexed keywords

1' EPI CRATERELLIN A; 4' OXOMACROPHORIN A; FARNESOL; MACROPHORIN A; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

ALNUS;

EID: 84908254751     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.09.075     Document Type: Article

References (38)

1. For reviews, see G. Mehta, and V. Singh Chem. Soc. Rev. 31 2002 324 334
2. L.F. Tietze, H.P. Bell, and S. Chandrasekhar Angew. Chem., Int. Ed. 42 2003 3996 4028 and references cited therein
3. M. Decker Curr. Med. Chem. 18 2011 1464 1475
4. T. Sassa, and H. Yoshikoshi Agric. Biol. Chem. 47 1983 187 189
5. T. Sassa, and M. Nukina Agric. Biol. Chem. 48 1984 1923 1925
6. W.A. Ayer, I.V. Altena, and L.M. Browne Phytochemistry 29 1990 1661 1665
7. T. Sassa, A. Ishizaki, M. Nukina, M. Ikeda, and T. Sugiyama Biosci., Biotechnol., Biochem. 62 1998 2260 2262
8. H. Fujimoto, E. Nakamura, Y.P. Kim, E. Okuyama, M. Ishibashi, and T. Sassa J. Nat. Prod. 64 2001 1234 1237
9. I.E. Mohamed, H. Gross, A. Pontius, S. Kehraus, A. Krick, G. Kelter, A. Maier, H.H. Fiebig, and G.M. König Org. Lett. 11 2009 5014 5017
10. L. Zhang, Y. Shen, F. Wang, Y. Leng, and J.-K. Liu Phytochemistry 71 2010 100 103
11. L.E. Schmidt, S.T. Deyrup, J. Baltrusaitis, D.C. Swenson, D.T. Wicklow, and J.B. Goler J. Nat. Prod. 73 2010 404 408
12. I.E. Mohamed, S. Kehraus, A. Krick, G.M. König, G. Kelter, A. Armin Maier, H.H. Fiebig, M. Kalesse, N.P. Malek, and H. Harald Gross J. Nat. Prod. 73 2010 2053 2056
13. H. Guo, T. Feng, H. Li, and J.K. Liu J. Asian Nat. Prod. Res. 14 2012 950 955 doi: 10.1080/10286020.2012.729508
14. X. Lin, X. Zhou, F. Wang, K. Liu, B. Yang, X. Yang, Y. Peng, J. Liu, Z. Ren, and Y. Liu Mar. Drugs 10 2012 106 115
15. S.-M. Fang, C.-B. Cui, C.-W. Li, C.-J. Wu, Z.-J. Zhang, L. Li, X.-J. Huang, and W.-C. Ye Mar. Drugs 10 2012 1266 1287
16. A. Hirose, H. Maeda, A. Tonouchi, T. Nehira, and M. Hashimoto Tetrahedron 70 2014 1458 1463
17. Y. Fu, P. Wu, J. Xue, and X. Wei J. Nat. Prod. 2014
18. G. Mehta, and K. Islam Tetrahedron Lett. 44 2003 3569 3572
19. G. Mehta, and K. Islam Org. Lett. 6 2004 807 810
20. G. Mehta, and S.C. Pan Org. Lett. 6 2004 811 813
21. G. Mehta, and S.S. Ramesh Tetrahedron Lett. 45 2004 1985 1987
22. G. Mehta, and K. Islam Tetrahedron Lett. 45 2004 3611 3615
23. G. Mehta, and S. Roy Org. Lett. 6 2004 2389 2392
24. G. Mehta, and S.C. Pan Org. Lett. 6 2004 3985 3988
25. G. Mehta, and K. Islam Tetrahedron Lett. 45 2004 7683 7687
26. G. Mehta, and S. Roy Tetrahedron Lett. 46 2005 7927 7930
27. G. Mehta, and S. Roy Chem. Commun. 2005 3210 3211
28. G. Mehta, S.R. Pujar, S.S. Ramesh, and K. Islam Tetrahedron Lett. 46 2005 3373 3376
29. G. Mehta, and S. Roy Tetrahedron Lett. 49 2008 1458 1460
30. G. Mehta, Y.C. Sunil Kumar, and T. Babu Khan Tetrahedron Lett. 51 2010 5112 5115
31. G. Mehta, Y.C. Sunil Kumar, and M. Das Tetrahedron Lett. 52 2011 3505 3508
32. G. Mehta, S. Roy, and S.C. Pan Tetrahedron Lett. 53 2012 4093 4095
33. G. Mehta, and M. Nagi Reddy J. Org. Chem. 78 2013 3367 3373
34. J. Vannada, L. Nieheus, B. König, and G. Mehta Tetrahedron 69 2013 6034 6040
35. H. Tanimoto, and T. Oritani Tetrahedron: Asymmetry 7 1996 1695 1704
36. C. Raptis, I.N. Lykakis, C. Tsangarakis, and M. Stratakis Chem. Eur. J. 15 2009 11918 11927
37. T. Laube, J.R. Schröder, R. Stehle, and K. Seifert Tetrahedron 58 2002 4299 4309
38. For a discussion on face selectivity during Diels-Alder reactions, see: G. Mehta, and R. Uma Acc. Chem. Res. 33 2000 278 286