Oxidative dearomatization of o -hydroxymethylphenol and intramolecular π4s+π2s Cycloaddition: An expedient synthesis of a tricyclic intermediate for platencin

Synlett

Volumn 24, Issue 12, 2013, Pages 1583-1587

  Singh, Vishwakarma ^a   Das, Beauty ^a   Mobin, Shaikhm ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY INDORE   (India)

Author keywords

cycloaddition; intramolecular Diels Alder reaction; oxidative dearomatization; spiroepoxycyclohexa 2,4 dienone

Indexed keywords

BENZYL DERIVATIVE; CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; HYDROXYL GROUP; ORTHO HYDROXYMETHYLPHENOL; PHENOL DERIVATIVE; PLATENCIN; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DECARBOXYLATION; DIELS ALDER REACTION; OXIDATION REDUCTION REACTION; PRECURSOR; STEREOCHEMISTRY; SYNTHESIS;

EID: 84879064997     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1339196     Document Type: Article

References (48)

1. Wang, J.; Soisson, S. M.; Young, K.; Shoop, W.; Kodali, S.; Galgoci, A.; Painter, R.; Parthasarathy, G.; Tang, Y. S.; Cummings, R.; Ha, S.; Dorso, K.; Motyl, M.; Jayasuriya, H.; Ondeyka, J.; Herath, K. B.; Zhang, C.; Hernandez, L.; Allocco, J.; Basilio, A.; Tormo, J. R.; Genilloud, O.; Vicente, F.; Pelaez, F.; Colwell, L.; Lee, S. H.; Michael, B.; Felcetto, T.; Gill, C.; Silver, L. L.; Hermes, J. D.; Batizal, K.; Barrett, J.; Schmatz, D.; Becker, J. W.; Cully, D.; Singh, S. B. Nature 2006, 441, 358
2. Singh, S. B.; Jayasuriya, H.; Ondeyka, J. G.; Herath, K. B.; Zhang, C.; Zink, D. L.; Tsou, N. N.; Ball, R. G.; Basilio, A.; Genilloud, O.; Diez, M. T.; Vicente, F.; Pelaez, F.; Young, K.; Wang, J. J. Am. Chem. Soc. 2006, 128, 11916.
3. Wang, J.; Kodali, S.; Lee, S. H.; Galgoci, A.; Painter, R.; Dorso, K.; Racine, F.; Motyl, M.; Hernandez, L.; Tinney, E.; Colletti, S. L.; Herath, K. B.; Cummings, R.; Salazar, O.; Gonzaalez, I.; Basilio, A.; Vicente, F.; Genilloud, O.; Pelaez, F.; Jayasuriya, H.; Young, K.; Cully, D. F.; Singh, S. B. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 7612.
4. Jayasuriya, H.; Herath, K. B.; Zhang, C.; Zink, D. L.; Basilio, A.; Genilloud, O.; Diez, M. T.; Vicente, F.; Gonzalez, I.; Salazar, O.; Pelaez, F.; Cummings, R.; Ha, S.; Wang, J.; Singh, S. B. Angew. Chem. Int. Ed. 2007, 46, 4684.
5. Palanichamy, K.; Kaliappan, K. P. Chem. Asian J. 2010, 5, 668
6. Nicolaou, K. C.; Li, A.; Edmonds, D. J. Angew. Chem. Int. Ed. 2006, 45, 7086
7. Nicolaou, K. C.; Edmonds, D. J.; Li, A.; Tria, G. S. Angew. Chem. Int. Ed. 2007, 46, 3942
8. Tiefenbacher, K.; Mulzer, J. Angew. Chem. Int. Ed. 2007, 46, 8074
9. Ghosh, A. K.; Xi, K. Org. Lett. 2007, 9, 4013.
10. Nicolaou, K. C.; Pappo, D.; Tsung, K. Y.; Gibe, R.; Chen, D. Y.-K. Angew. Chem. Int. Ed. 2008, 47, 944.
11. Tiefenbacher, K.; Mulzer, J. Angew. Chem. Int. Ed. 2008, 47, 2548
12. Magnus, P.; Rivera, H.; Lynch, V. Org. Lett. 2010, 12, 5677
13. Eey, S. T.-C.; Lear, M. J. Org. Lett. 2010, 12, 5510
14. Oblak, E. Z.; Wright, D. L. Org. Lett. 2011, 13, 2263.
15. Nicolaou, K. C.; Tria, G. S.; Edmonds, D. J. Angew. Chem. Int. Ed. 2008, 47, 1780
16. Hayashida, J.; Rawal, V. H. Angew. Chem. Int. Ed. 2008, 47, 4373
17. Tiefenbacher, K.; Mulzer, J. Angew. Chem. Int. Ed. 2008, 47, 6199.
18. Nicolaou, K. C.; Toh, Q.-Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2008, 130, 11292
19. Austin, K. A. B.; Banwell, M. G.; Willis, A. C. Org. Lett. 2008, 10, 4465.
20. Tiefenbacher, K.; Mulzer, J. J. Org. Chem. 2009, 74, 2937
21. Varseev, G. N.; Maier, M. E. Angew. Chem. Int. Ed. 2009, 48, 3685
22. Ghosh, A. K.; Xi, K. Angew. Chem. Int. Ed. 2009, 48, 5372.
23. Li, P.; Yamamoto, H. Chem. Commun. 2010, 46, 6294.
24. Singh, V.; Sahu, B. C.; Bansal, V.; Mobin, S. M. Org. Biomol. Chem. 2010, 8, 4472
25. Palanichamy, K.; Subrahmanyam, A. V.; Kaliappan, K. P. Org. Biomol. Chem. 2011, 9, 7877
26. Yoshimitsu, T.; Nojima, S.; Hashimoto, M.; Tanaka, T. Org. Lett. 2011, 13, 3698
27. Wang, J.; Sintim, H. O. Chem. Eur. J. 2011, 17, 3352
28. Hirai, S.; Nakada, M. Tetrahedron 2011, 67, 518.
29. Nicolaou, K. C.; Chen, J. S. Chem. Soc. Rev. 2009, 38, 2993
30. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010
31. Poulin, J.; Grise-Bard Barriault, L. Chem. Soc. Rev. 2009, 38, 3092
32. Vo, N. T.; Pace, R. D. M.; O'hara, F.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 404
33. Constantin, M.-A.; Conrad, J.; Merisor, E.; Koschorreck, K.; Urlacher, V. B.; Beifuss, U. J. Org. Chem. 2012, 77, 4528.
34. Quideau, S.; Pouysegu, L.; Deffieux, D. Synlett 2008, 467
35. Pouysegu, L.; Chassaing, S.; Dejugnac, D.; Lamidey, A.-M.; Miqueu, K.; Sotiropoulos, J.-M.; Quideau, S. Angew. Chem. Int. Ed. 2008, 47, 3552
36. Luo, S.-Y.; Jang, Y.-J.; Liu, J.-Y.; Chu, C.-S.; Liao, C.-C.; Hung, S.-C. Angew. Chem. Int. Ed. 2008, 47, 8082
37. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383.
38. Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856
39. Gesson, J.-P.; Hervaud, L.; Mondon, M. Tetrahedron Lett. 1993, 34, 2941.
40. Singh, V. Acc. Chem. Res. 1999, 32, 324
41. Singh, V.; Praveena, J. D.; Karki, K.; Mobin, S. M. J. Org. Chem. 2007, 72, 2058
42. Singh, V.; Bhalerao, P.; Mobin, S. M. Tetrahedron Lett. 2010, 51, 3337
43. Singh, V.; Sahu, P. K.; Sahu, B. C.; Mobin, S. M. J. Org. Chem. 2009, 74, 6092.
44. Singh, V.; Bhalerao, P.; Mobin, S. M. Tetrahedron 2012, 68, 238
45. Singh, V.; Bhalerao, P.; Sahu, B. C.; Mobin, S. M. Tetrahedron 2013, 69, 137.
46. Suzuki, M.; Sugiyama, T.; Watanabe, M.; Murayama, T.; Yamashita, K. Agric. Biol. Chem. 1987, 51, 1121.
47. Singh, V.; Thomas, B. J. Org. Chem. 1997, 62, 5310.
48. Singh, V.; Thomas, B. Chem. Commun. 1992, 1211. Technology