Microwave-assisted Diels-Alder reaction of 1,3,3- trimethyl-2-vinyl-1- cyclohexene with chromones An expeditious approach to analogues of the puupehenone group of marine diterpenoids and kampanols

Canadian Journal of Chemistry

Volumn 88, Issue 12, 2010, Pages 1233-1239

  Kamble, Rajesh M ^a   Ramana, M M V ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

Chromones; Diels Alder; Microwave synthesis; Regioselectivity; Stereoselectivity; TiCl4

Indexed keywords

CHROMONES; CYCLOHEXENES; DIELS-ALDER; DIELS-ALDER REACTION; DITERPENOIDS; MICROWAVE SYNTHESIS; MICROWAVE-ASSISTED; TICL4; TRIMETHYL;

LIPIDS; MICROWAVE IRRADIATION; OLEFINS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

EID: 78650507336     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V10-137     Document Type: Article

References (49)

1. Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93 (2), 741. 10.1021/cr00018a006
2. Loperfido, J. C. J. Org. Chem. 1973, 38 (2), 399. 10.1021/jo00942a044
3. Brieger, G. Tetrahedron Lett. 1965, 6 (49), 4429. 10.1016/S0040-4039(00) 71682-0
4. Hollinshead, D. M.; Howell, S. C.; Ley, S. V.; Mahon, M.; Ratcliffe, N. M.; Worthington, P. A. J. Chem. Soc., Perkin Trans. 1 1983, 7, 1579. 10.1039/p19830001579
5. Engler, T. A.; Naganathan, S.; Takusagawa, F.; Yohannes, D. Tetrahedron Lett. 1987, 28 (44), 5267. 10.1016/S0040-4039(00)96704-2
6. Engler, T. A.; Sampath, U.; Vander Velde, D.; Takusagawa, F. Tetrahedron 1992, 48 (43), 9399. 10.1016/S0040-4020(01)88309-5
7. Engler, T. A.; Naganathan, S. Tetrahedron Lett. 1986, 27 (9), 1015. 10.1016/S0040-4039(86)80036-3
8. Engler, T. A.; Sampath, U.; Naganathan, S.; Vander Velde, D.; Takusagawa, F.; Yohannes, D. J. Org. Chem. 1989, 54 (24), 5712. 10.1021/jo00285a018 (Pubitemid 20044203)
9. Knol, J.; Meetsma, A.; Feringa, B. L. Tetrahedron Asymmetry 1995, 6 (5), 1069. 10.1016/0957-4166(95)00127-B
10. Gorgues, A.; Stephan, D.; Khanous, A. B. A.; Co, A. L. Tetrahedron 1990, 46 (8), 2817. 10.1016/S0040-4020(01)88374-5
11. Carreo, M. C.; Garca Ruano, J. L.; Toledo, M. A. Chem. Eur. J. 2000, 6 (2), 288. 10.1002/(SICI)1521-3765(20000117)6:2<288::AID-CHEM288>3.0.CO;2-2
12. Mayelvaganan, T.; Hadimani, S.; Bhat, S. V. Tetrahedron 1997, 53 (6), 2185. 10.1016/S0040-4020(96)01120-9 (Pubitemid 27065201)
13. Hsung, R. P. J. Org. Chem. 1997, 62 (23), 7904. 10.1021/jo971479p
14. Ghosh, C. K.; Bhattacharyya, A.; Bandyopadhyay, C. J. Chem. Soc. Chem. Commun. 1984, 1319. 10.1039/c39840001319
15. Cremins, P. J.; Saengchantara, T.; Wallace, T. W. Tetrahedron 1987, 43 (13), 3075. 10.1016/S0040-4020(01)86849-6
16. Epiotis, N. D.; Shaik, S. J. Am. Chem. Soc. 1978, 100 (1), 1. 10.1021/ja00469a001
17. Branchadell, V.; Oliva, A.; Bertran, J. J. Mol. Struct. Theochem 1986, 138 (1-2), 117. 10.1016/0166-1280(86)87014-2
18. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976.
19. Kappe, C. O. Angew. Chem. 2004, 43 (46), 6250. 10.1002/anie.200400655 (Pubitemid 40036603)
20. Gedye, R.; Rank, W.; Westaway, K. Can. J. Chem. 1991, 69 (4), 706. 10.1139/v91-106
21. Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Jimenez, J. L.; Palacios, J. C.; Sanchez, J. B. J. Org. Chem. 1999, 64 (17), 6297. 10.1021/jo990442x (Pubitemid 29404504)
22. Kaval, N.; Van der Eycken, J.; Caroen, J.; Dehaen, W.; Strohmeier, G. A.; Kappe, C. O.; Van der Eycken, E. J. Comb. Chem. 2003, 5 (5), 560. 10.1021/cc0300098 (Pubitemid 37206160)
23. Ravi, B. N.; Perzanowski, H. P.; Ross, R. A.; Erdman, T. R.; Scheuer, P. J.; Finer, J.; Clardy, J. Pure Appl. Chem. 1979, 51 (9), 1893. 10.1351/pac197951091893
24. Amade, P.; Chevelot, L.; Perzanowski, H. P.; Scheuer, P. J. Helv. Chim. Acta 1983, 66 (6), 1672. 10.1002/hlca.19830660606
25. Kohmoto, S.; McConnell, O. J.; Wright, A.; Koehn, F.; Thompson, W.; Lui, M.; Snader, K. M. J. Nat. Prod. 1987, 50 (2), 336. 10.1021/np50050a064
26. Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1993, 58 (24), 6565. 10.1021/jo00076a012 (Pubitemid 24011161)
27. Nasu, S. S.; Yeung, B. K. S.; Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M.; Goins, K. J. Org. Chem. 1995, 60 (22), 7290. 10.1021/jo00127a039
28. Urban, S.; Capon, R. J. J. Nat. Prod. 1996, 59 (9), 900. 10.1021/np9603838 (Pubitemid 26337518)
29. Djura, P.; Stierle, D. B.; Sullivan, B.; Faulkner, D. J.; Arnold, E.; Clardy, J. J. Org. Chem. 1980, 45 (8), 1435. 10.1021/jo01296a019 (Pubitemid 10027110)
30. Hamann, M. T.; Scheuer, P. J. Tetrahedron Lett. 1991, 32 (41), 5671. 10.1016/S0040-4039(00)93525-1
31. Kazlauskas, R.; Murphy, P. T.; Warren, R. G.; Wells, R. J.; Blount, J. F. Aust. J. Chem. 1978, 31 (12), 2685. 10.1071/CH9782685
32. Capon, R. J. Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995; Vol. 15.
33. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortes, M.; Armstrong, V. Tetrahedron 1999, 55 (52), 15181. 10.1016/S0040-4020(99)00992-8
34. Bourguet-Kondracki, M. L.; Lacombe, F.; Guyot, M. J. Nat. Prod. 1999, 62 (9), 1304. 10.1021/np9900829 (Pubitemid 29463335)
35. El Sayed, K. A.; Bartyzel, P.; Shen, X.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Tetrahedron 2000, 56 (7), 949. 10.1016/S0040-4020(99)01093-5 (Pubitemid 30094161)
36. Takamatsu, S.; Hodges, T. W.; Rajbhandari, I.; Gerwick, W. H.; Hamann, M. T.; Nagle, D. G. J. Nat. Prod. 2003, 66 (5), 605. 10.1021/np0204038 (Pubitemid 36617880)
37. El Sayed, K. A.; Dunbar, D. C.; Perry, T. L.; Wilkins, S. P.; Hamann, T.; Greenplate, J. T.; Wideman, M. A. J. Agric. Food Chem. 1997, 45 (7), 2735. 10.1021/jf960746+
38. Singh, S. B.; Zink, D. L.; Williams, M.; Polishook, J. D.; Sanchez, M.; Silverman, K. C.; Lingham, R. B. Bioorg. Med. Chem. Lett. 1998, 8 (16), 2071. 10.1016/S0960-894X(98)00371-0 (Pubitemid 28561581)
39. Bhar, S. S.; Ramana, M. M. V. J. Org. Chem. 2004, 69 (25), 8935. 10.1021/jo049616n (Pubitemid 39603058)
40. Jones, G. H.; Mackenzie, J. B. D.; Robertson, A.; Whalley, W. B. J. Chem. Soc. 1949, 562. 10.1039/jr9490000562
41. Wiley, P. F. US Patent 2,621,189, December 9,1952; Chem. Abstr. 1953, 47, 10011h.
42. Chiji, H.; Aiba, T.; Izawa, M. Agric. Biol. Chem. 1978, 42 (1), 159.
43. Da Re, P. Farmaco (Pavia). Ed. Sci. 1956, 11, 662;
44. Chem. Abstr. 1959, 53, 122101.
45. Badcock, G. G.; Dean, F. M.; Robertson, A.; Whalley, W. B. J. Chem. Soc. 1950, 903. 10.1039/jr9500000903
46. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman: Essex, England, 1994.
47. Schonberg, A.; Sina, A. J. Am. Chem. Soc. 1950, 72 (8), 3396. 10.1021/ja01164a022
48. Materials Studio, v4.4.0.0030, Accelrys Software Inc.: San Diego, 2008.
49. Pritchard, R. G.; Sheldrake, H. M.; Taylor, I. Z.; Wallace, T. W. Tetrahedron Lett. 2008, 49 (26), 4156. 10.1016/j.tetlet.2008.04.114