Azadiene Diels-Alder cycloaddition of fulvenes: A facile approach to the [1]pyrindine system

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3453-3456

  Hong, Bor Cherng ^a   Wu, Jian Lin ^a   Gupta, Arun Kumar ^a   Hallur, Mahanandeesha Siddappa ^a   Liao, Ju Hsiou ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALKENE DERIVATIVE; N SULFONYL 1 AZA 1,3 BUTADIENE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ELECTRON; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 6444238096     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048762c     Document Type: Article

References (53)

1. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
2. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
3. For recent reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259. (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
4. For examples, see: (a) Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974. (b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839. (c) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713. (d) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733. (e) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
5. For examples, see: (a) Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974. (b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839. (c) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713. (d) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733. (e) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
6. For examples, see: (a) Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974. (b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839. (c) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713. (d) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733. (e) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
7. For examples, see: (a) Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974. (b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839. (c) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713. (d) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733. (e) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
8. For examples, see: (a) Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974. (b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839. (c) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713. (d) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733. (e) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
9. (a) Rawson, D. I.; Carpenter, B. K.; Hoffmann, H. M. J. Am. Chem. Soc. 1979, 101, 1786.
10. (b) Noyori, R.; Hayakawa, Y.; Takaya, H.; Murai, S.; Kobayashi, R.; Sonoda, N. J. Am. Chem. Soc. 1978, 100, 1759.
11. (a) Imafuku, K.; Arai, K. Synthesis 1989, 501.
12. (b) Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201.
13. (a) Harre, M.; Raddatz, P.; Walenta R.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 480.
14. (b) Gleiter R.; Borzyk, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
15. (a) Himeda, Y.; Yamataka, H.; Ueda I.; Hatanaka, M. J. Org. Chem. 1997, 62, 6529.
16. (b) Nair, V.; Nair, A. G.; Radhakrishnan, K. V. Nandakumar, M. V.; Rath, N. P. Synlett 1997, 767.
17. (a) Gupta, Y. N.; Doa, M. J.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7336.
18. (b) Yoshida, Z.-I.; Shibata, M.; Ogino, E.; Sugimoto, T. Angew. Chem., Int. Ed. Engl. 1985, 24, 60.
19. (a) For an example of an intermolecular [6 + 2] cycloaddition, see: Hong, B. C.; Shr, Y. J.; Wu, J. L.; Gupta, A. K.; Lin, K. J. Org. Lett. 2002, 4, 2249.
20. (b) For an example of an intramolecular [6 + 2] cycloaddition, see: Suda, M.; Hafner, K. Tetrahedron Lett. 1977, 2453.
21. (c) Wu T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308.
22. Barluenga, J.; Martinez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2001, 123, 11113.
23. (a) Theoretically, the Diels-Alder reaction of isoxazole with alkenes should not proceed; see: Gonzãlez, J.; Taylor, E. C.; Houk, K. N. J. Org. Chem. 1992, 57, 3753.
24. (b) A low-yielding [4 + 2] cycloaddition of isoxazole has been reported; see: Nesi, R.; Giomi, D.; Papaleo, S.; Turchi, S. J. Org. Chem. 1992, 57, 3713.
25. (c) A low-yielding [4 + 2] cycloaddition of triazine has been reported; see: Diaz-Ortiz, A.; Hoz, A.; Prieto, P.; Carrillo, J. R.; Moreno, A.; Neunhoeffer, H. Synlett 2001, 236.
26. Hong, B.-C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H. Tetrahedron Lett. 2004, 45, 1663.
27. Hong, B.-C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H.; Lee, H.-H. Org. Lett. 2003, 5, 1689.
28. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249. (b) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663.
29. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249. (b) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663.
30. (a) Streptazolin, streptazon C, and streptazon A were isolated from Streptomyces FORM5, Stain A1, viridochromogenes and leteogriseus. See: (i) Puder, C.; Krastel, P.; Zeeck, A. J. Nat. Prod. 2000, 63, 1258. (ii) Puder. C.; Loya, S.; Hizi, A.; Zeeck, A. J. Nat. Prod. 2001, 64, 42. (iii) Grabley, S.; Kluge, H.; Hoppe, H.-U. Angew. Chem. 1987, 99, 692.
31. (a) Streptazolin, streptazon C, and streptazon A were isolated from Streptomyces FORM5, Stain A1, viridochromogenes and leteogriseus. See: (i) Puder, C.; Krastel, P.; Zeeck, A. J. Nat. Prod. 2000, 63, 1258. (ii) Puder. C.; Loya, S.; Hizi, A.; Zeeck, A. J. Nat. Prod. 2001, 64, 42. (iii) Grabley, S.; Kluge, H.; Hoppe, H.-U. Angew. Chem. 1987, 99, 692.
32. (a) Streptazolin, streptazon C, and streptazon A were isolated from Streptomyces FORM5, Stain A1, viridochromogenes and leteogriseus. See: (i) Puder, C.; Krastel, P.; Zeeck, A. J. Nat. Prod. 2000, 63, 1258. (ii) Puder. C.; Loya, S.; Hizi, A.; Zeeck, A. J. Nat. Prod. 2001, 64, 42. (iii) Grabley, S.; Kluge, H.; Hoppe, H.-U. Angew. Chem. 1987, 99, 692.
33. (b) Abikoviromycin was isolated from Isolierung aus Streptomyces-Arten. See: (i) Sakagami, Y.; Utahara, R.; Yagishita, K.; Umezawa, H. J. Antibiot. 1958, 11, 231. (ii) Gurevich, A. I.; Kolosov, M. N.; Korobko, V. G.; Onoprienko, V. V. Tetrahedron Lett. 1968, 9, 2209. (iii) Maruyama, H.; Okamoto, S.; Kubo, Y.; Tsuji, G.; Fujii, I.; Ebizuka, Y.; Furihata, K.; Hayakawa, Y.; Nagasawa, H.; Sakuda, S. J. Antibiot. 2003, 56, 801.
34. (b) Abikoviromycin was isolated from Isolierung aus Streptomyces-Arten. See: (i) Sakagami, Y.; Utahara, R.; Yagishita, K.; Umezawa, H. J. Antibiot. 1958, 11, 231. (ii) Gurevich, A. I.; Kolosov, M. N.; Korobko, V. G.; Onoprienko, V. V. Tetrahedron Lett. 1968, 9, 2209. (iii) Maruyama, H.; Okamoto, S.; Kubo, Y.; Tsuji, G.; Fujii, I.; Ebizuka, Y.; Furihata, K.; Hayakawa, Y.; Nagasawa, H.; Sakuda, S. J. Antibiot. 2003, 56, 801.
35. (b) Abikoviromycin was isolated from Isolierung aus Streptomyces-Arten. See: (i) Sakagami, Y.; Utahara, R.; Yagishita, K.; Umezawa, H. J. Antibiot. 1958, 11, 231. (ii) Gurevich, A. I.; Kolosov, M. N.; Korobko, V. G.; Onoprienko, V. V. Tetrahedron Lett. 1968, 9, 2209. (iii) Maruyama, H.; Okamoto, S.; Kubo, Y.; Tsuji, G.; Fujii, I.; Ebizuka, Y.; Furihata, K.; Hayakawa, Y.; Nagasawa, H.; Sakuda, S. J. Antibiot. 2003, 56, 801.
36. (c) Pyrindicin was isolated from Streptomyces sp. SCC 2313. See: Hegde, V. R.; Dai, P.; Patel, M. G.; Troyanovich, J. J.; Das, P.; Puar, M. S. J. Antibiot. 1994, 47, 110.
37. (d) trans-5,7-Dimethyl-6,7-dihydro-5H-[1]pyrindine was isolated from aus Erdoel. See: Monti, S. A.; Schmidt, R. R.; Shoulders, B. A.; Lochte, H. L. J. Org. Chem. 1972, 37, 3834.
38. (e) Octahydro-[1]pyrindine-3,4,5-triol was Isolation from Rhizoctonia leguminicola. See: Guengerich, F. P.; DiMari, S, J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055.
39. (f) 1-Methyl-4-azafluorenone was isolated from branches of Porcelia macrocarpa (Warm.). See: Chaves, M. H.; Santos, L. de A.; Lago, J. H. G.; Roque, N. F. J. Nat. Prod. 2001, 64, 40.
40. Several synthetic approaches to streptazolins have been reported. (a) For 8α-hydroxystreptazolone, see: Izumi Nomura, I.; Mukai, C. J. Org. Chem. 2004, 69, 1803. (b) For streptazolin, see: Kozikowski, A. P.; Park, P. J. Am. Chem. Soc. 1985, 107, 1763.
41. Several synthetic approaches to streptazolins have been reported. (a) For 8α-hydroxystreptazolone, see: Izumi Nomura, I.; Mukai, C. J. Org. Chem. 2004, 69, 1803. (b) For streptazolin, see: Kozikowski, A. P.; Park, P. J. Am. Chem. Soc. 1985, 107, 1763.
42. 2; 60% yield), see: Boger, D. L.; Curran, T. T. J. Org. Chem. 1990, 55, 5439 and ref 2c.
43. For other regioselective [2 + 4] cycloadditions of fulvenes to electron-deficient dienes, see: (a) Houk, K. N.; Luskus, L. J. J. Org. Chem. 1973, 38, 3836. (b) Bimanand, A. Z.; Gupta, Y. N.; Doa, M. J.; Eaton, T. A.; Houk, K. N. J. Org. Chem. 1983, 48, 403. (c) Lewis, N. J.; Collins, W. J.; Knight, D. B. J. Med. Chem. 1979, 22, 1505. (d) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Sheela, K. C.; Rath, N. P. Tetrahedron 1997, 53, 17361.
44. For other regioselective [2 + 4] cycloadditions of fulvenes to electron-deficient dienes, see: (a) Houk, K. N.; Luskus, L. J. J. Org. Chem. 1973, 38, 3836. (b) Bimanand, A. Z.; Gupta, Y. N.; Doa, M. J.; Eaton, T. A.; Houk, K. N. J. Org. Chem. 1983, 48, 403. (c) Lewis, N. J.; Collins, W. J.; Knight, D. B. J. Med. Chem. 1979, 22, 1505. (d) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Sheela, K. C.; Rath, N. P. Tetrahedron 1997, 53, 17361.
45. For other regioselective [2 + 4] cycloadditions of fulvenes to electron-deficient dienes, see: (a) Houk, K. N.; Luskus, L. J. J. Org. Chem. 1973, 38, 3836. (b) Bimanand, A. Z.; Gupta, Y. N.; Doa, M. J.; Eaton, T. A.; Houk, K. N. J. Org. Chem. 1983, 48, 403. (c) Lewis, N. J.; Collins, W. J.; Knight, D. B. J. Med. Chem. 1979, 22, 1505. (d) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Sheela, K. C.; Rath, N. P. Tetrahedron 1997, 53, 17361.
46. For other regioselective [2 + 4] cycloadditions of fulvenes to electron-deficient dienes, see: (a) Houk, K. N.; Luskus, L. J. J. Org. Chem. 1973, 38, 3836. (b) Bimanand, A. Z.; Gupta, Y. N.; Doa, M. J.; Eaton, T. A.; Houk, K. N. J. Org. Chem. 1983, 48, 403. (c) Lewis, N. J.; Collins, W. J.; Knight, D. B. J. Med. Chem. 1979, 22, 1505. (d) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Sheela, K. C.; Rath, N. P. Tetrahedron 1997, 53, 17361.
47. TinyClave (Büchiglassuster) is a miniature laboratory autoclave for safe small-scale experiment under pressure. It allows one to run chemical reactions in organic media under pressure up to 10 bar and 150°C.
48. Selectivity may also be explained by the LUMO (azadiene) and HOMO (fulvene) coefficients; see ref 2c.
49. Croce, P.; Ferraccioli, R.; Rosa, C. L. J. Chem. Soc., Perkin Trans. 1 1994, 2499.
50. 2, 78%); see: Marchand, E.; Morel, G.; Sinbandhit, S. Eur. J. Org. Chem. 1942, 7, 1729.
51. 13C NMR, DEPT, IR, MS, and HRMS. In most cases, COSY and HMQC spectra were also obtained. Yields refer to spectroscopically and chromatographically homogeneous (>95%) materials.
52. 2)].
53. 2)].