Enantioselective syntheses of bioactive epoxyquinone natural products (+)-harveynone and (-)-asperpentyn

Tetrahedron Letters

Volumn 53, Issue 32, 2012, Pages 4093-4095

  Mehta, Goverdhan ^a,b   Roy, Subhrangsu ^a   Pan, Subhas Chandra ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

Enantioselective total synthesis; Epoxyquinone natural products; Retro Diels Alder reaction; Sonogashira coupling

Indexed keywords

ASPERPENTYN; HARVEYNONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; SYNTHESIS;

ALNUS;

EID: 84863612741     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.115     Document Type: Article

References (44)

1. For reviews see: J. Marco-Contelles, M.T. Molina, and S. Anjum Chem. Rev. 104 2004 2857 2899
2. M. Shoji Bull. Chem. Soc. Jpn. 80 2007 1672 1690
3. K. Miyashita, and T. Imanishi Chem. Rev. 105 2005 4515 4536
4. S. Sakamura, J. Ito, and R. Sakai Agric. Biol. Chem. 34 1970 153 155
5. J.Y. Li, J.K. Harper, D.M. Grant, B.O. Tombe, B. Bashyal, W.M. Hess, and G.A. Strobel Phytochemistry 56 2001 463 468
6. A. Gehrt, G. Erkel, T. Anke, and O. Sterner J. Antibiot. 51 1998 455 463
7. J.C. Lee, G.A. Strobel, E. Lobkovsky, and J. Clardy J. Org. Chem. 61 1996 3232 3233
8. G. Ding, F. Zhang, H. Chen, L. Guo, Z. Zou, and Y. Che J. Nat. Prod. 74 2011 286 291
9. Selected lead references towards the synthesis of epoxyquinone natural products: M. Shoji, J. Yamaguchi, H. Kakeya, H. Osada, and Y. Hayashi Angew. Chem., Int. Ed. 41 2002 3192 3194
10. C. Li, S. Bardhan, E.A. Pace, M.-C. Liang, T.D. Gilmore, and J.A. Porco Org. Lett. 4 2002 3267
11. J.A. Porco, S. Su, X. Lei, S. Bardhan, and S.D. Rychnovsky Angew. Chem., Int. Ed. 45 2006 5790 5792
12. M. Matsuzawa, H. Kakeya, J. Yamaguchi, M. Shoji, R. Onose, H. Osada, and Y. Hayashi Chem. Asian. J. 1 2006 845 851
13. J. Li, and D. Lee Chem. Asian. J. 5 2010 1298 1302
14. D.R. Hookins, A.R. Burns, and R.J.K. Taylor Eur. J. Org. Chem. 2011 451 454
15. Syntheses related to harveynone and/or asperpentyne: T. Kamikubo, and K. Ogaswara Chem. Commun. 1996 1679 1680
16. A.E. Graham, D. McKerrecher, D.H. Davies, and R.J.K. Taylor Tetrahedron Lett. 37 1996 7445 7448
17. A.E. Graham, and R.J.K. Taylor J. Chem. Soc., Perkin Trans. 1 1997 1087 1089
18. T. Kamikubo, and K. Ogaswara Heterocycles 47 1998 69 72
19. M.W. Miller, and C.R. Johnson J. Org. Chem. 62 1997 1582 1583
20. E.-I. Negishi, Z. Tan, S.-Y. Liou, and B. Liao Tetrahedron 56 2000 10197 10207
21. M.T. Barros, C.D. Maycock, and M.R. Ventura Chem. Eur. J. 6 2000 3991 3996
22. T. Tachihara, and T. Kitahara Tetrahedron 59 2003 1773 1780
23. M.C. Carreño, E. Merino, M. Ribagorda, Á. Somoza, and A. Urbano Chem. Eur. J. 13 2007 1064 1077
24. J. Li, S. Park, R.L. Miller, and D. Lee Org. Lett. 11 2009 571 574
25. D.M. Pinkerton, M.G. Banwell, and A.C. Willis Org. Lett. 11 2009 4290 4293
26. D. Hookins, and R.J.K. Taylor Tetrahedron Lett. 51 2010 6619 6621
27. For synthetic work towards diverse epoxyquinone natural products from our group, see: G. Mehta, and K. Islam Tetrahedron Lett. 44 2003 3569 3572
28. G. Mehta, and K. Islam Org. Lett. 6 2004 807 810
29. G. Mehta, and S.C. Pan Org. Lett. 6 2004 811 813
30. G. Mehta, and S.S. Ramesh Tetrahedron Lett. 45 2004 1985 1987
31. G. Mehta, and K. Islam Tetrahedron Lett. 45 2004 3611 3615
32. G. Mehta, and S. Roy Org. Lett. 6 2004 2389 2392
33. G. Mehta, and S.C. Pan Org. Lett. 6 2004 3985 3988
34. G. Mehta, and K. Islam Tetrahedron Lett. 45 2004 7683 7687
35. G. Mehta, and S. Roy Tetrahedron Lett. 46 2005 7927 7930
36. G. Mehta, and S. Roy Chem. Commun. 2005 3210 3211
37. G. Mehta, S.R. Pujar, S.S. Ramesh, and K. Islam Tetrahedron Lett. 46 2005 3373 3376
38. G. Mehta, and S. Roy Tetrahedron Lett. 49 2008 1458 1460
39. G. Mehta, Y.C. Sunil Kumar, and T.B. Khan Tetrahedron Lett. 51 2010 5112 5115
40. T. Nagata, Y. Ando, and A. Hirrota Biosci., Biotechnol., Biochem. 56 1992 810 811
41. K. Kawazu, A. Kobayashi, and K. Oe Chem. Abstr. 115 1991 181517
42. A. Muhlenfeld, and H. Achenbach Phytochemistry 27 1988 3853 3855
43. S. Klaiklay, V. Ruckachairsirikul, K. Tadpetch, Y. Sukpondma, A. Phongpaichit, J. Buatong, and J. Sakayaroj Tetrahedron 68 2012 2299 2305
44. L. Garlaschelli, E. Magisrali, G. Vidari, and O. Zuffardi Tetrahedron Lett. 36 1995 5633 5636