Investigating direct access to 2-oxospiro[4.5]decanones via 6π-electrocyclisation

European Journal of Organic Chemistry

Volumn , Issue 28, 2007, Pages 4699-4705

  Pouwer, Rebecca H ^a   Schill, Heiko ^a   Williams, Craig M ^a   Bernhardt, Paul V ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

2 oxospiro 4.5 decan 1 one; Calculations; Electrocyclic reactions; Microwave irradiation; Spirolactones

Indexed keywords

EID: 35348850316     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700367     Document Type: Article

References (41)

1. E. Caloprisco, J.-D. Fourneron, R. Faure, F. E. Demarne, J. Agric. Food Chem. 2002, 50, 78-80.
2. M. C. De La Torre, C. Pascual, B. Rodriguez, F. Piozzi, G. Savona, A. Perales, Phytochemistry 1986, 25, 1397-1403.
3. A. T. Merritt, S. V. Ley, Nat. Prod. Rep. 1992, 9, 243-287.
4. A. Srikrishna, S. Nagaraju, G. V. R. Sharma, J. Chem. Soc. Chem. Commun. 1993, 285-288.
5. H.-J. Liu, J.-L. Zhu, I.-C. Chen, R. Jankowska, Y. Han, K.-S. Shia, Angew. Chem. Int. Ed. 2003, 42, 1851-1853.
6. E. Wenkert, M. E. Alonso, B. L. Buckwalter, K. J. Chou, J. Am. Chem. Soc. 1977, 99, 4778-4782.
7. A. J. Pearson, M. W. Zettler, J. Am. Chem. Soc. 1989, 111, 3908-3918.
8. B. Frey, A. P. Wells, D. H. Rogers, L. N. Mander, J. Am. Chem. Soc. 1998, 120, 1914-1915.
9. N. Pérez-Hernández, M. Fehles, C. Pérez, R. Pérez, M. L. Rodriguez, C. Foces-Foces, J. D. Martin, J. Org. Chem. 2006, 71, 1139-1151.
10. H. Rudler, P. Harris, A. Parlier, F. Cantagrel, B. Denise, M. Bellassoued, J. Vaissermann, J. Organomet. Chem. 2001, 624, 186-202.
11. C. Kuroda, T. Kasahara, K. Akiyama, T. Amemiya, T. Kunishima, Y. Kimura, Tetrahedron 2002, 58, 4493-4504.
12. V. Maslak, R. Matović, R. N. Saičić, Tetrahedron 2004, 60, 8957-8966.
13. A. Hassner, T. K. Pradhan, Tetrahedron Lett. 2006, 47, 5511-5513.
14. E. M. Peterson, K. Xu, K. D. Holland, A. C. McKeon, S. M. Rothman, J. A. Ferrendelli, D. F. Covey, J. Med. Chem. 1994, 37, 275-286.
15. M. E. Jung, C. N. Zimmerman, G. T. Lowen, S. I. Khan, Tetrahedron Lett. 1993, 34, 4453-4456.
16. M. Periasamy, M. R. Reddy, U. Radhakrishnan, A. Devasagayaraj, J. Org. Chem. 1993, 58, 4997-4999.
17. R. B. Woodward, R. Hoffmann, Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
18. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry; VCH: Weinheim, 1970.
19. W. H. Okamura, A. R. De Lera, Comprehensive Organic Synthesis (Ed.: B. Trost); Pergamon: Oxford, 1991; Vol. 5, p. 699.
20. T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165.
21. M. W. Miller, C. R. Johnson, J. Org. Chem. 1997, 62, 1582-1583.
22. K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49.
23. J.-L. Luche, J. Am. Chem. Soc. 1978, 100, 2226.
24. R. Srinivasan, V. Y. Merritt, J. N. C. Hsu, P. H. G. Op Het Veld, W. H. Laarhoven, J. Org. Chem. 1978, 43, 980-985.
25. P. K. Datta, C. Yau, T. S. Hooper, B. L. Yvon, J. L. Charlton, J. Org. Chem. 2001, 66, 8606-8611, and references cited therein.
26. S. Samori, M. Hara, T.-I. Ho, S. Tojo, K. Kawai, M. Endo, M. Fujitsuka, T. Majima, J. Org. Chem. 2005, 70, 2708-2712.
27. T.-Q. Yu, Y. Fu, L. Liu, Q.-X. Guo, J. Org. Chem. 2006, 71, 6157-6164.
28. C. M. Williams, L. N. Mander, Tetrahedron 2001, 57, 425-447.
29. M. Mella, M. Freccero, A. Albini, J. Am. Chem. Soc. 1996, 118, 10311-10312.
30. R. H. Bradbury, T. L. Gilchrist, C. W. Rees, J. Chem. Soc. Perkin Trans. 1 1981, 3234-3238.
31. All calculations were performed with the Gaussian program package: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. AlLaham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Wallingford CT, 2004.
32. V. Guner, K. S. Khuong, A. G. Leach, P. S. Lee, M. D. Bartberger, K. N. Houk, J. Phys. Chem. A 2003, 107, 11445-11459.
33. D. H. Ess, K. N. Houk, J. Phys. Chem. A 2005, 109, 9542-9553.
34. J. W. Ochterski, http://www.gaussian.com/g_whitepap/thermo.htm; last accessed: 2007-06-28.
35. The [1,5]-H shift products 76-78 and 56, 85, and 86 were calculated stemming from a thermal process instead of the photochemical since the latter should be disfavoured and the thermal activation energy could also be provided by the irradiation. The transition states for these thermal [1,5]-H shifts and the energies thereof have not been calculated, but should be similar to the values obtained for the thermal rearrangement of the thermally induced cyclisation products.
36. J. E. Baldwin, B. R. Chapman, J. Org. Chem. 2005, 70, 377-380.
37. J. R. de Dobbelaere, E. L. van Zeeventer, J. W. de Haan, H. M. Buck, Theor. Chim. Acta 1975, 38, 241-244.
38. B. A. Hess Jr, J. E. Baldwin, J. Org. Chem. 2002, 67, 6025-6033.
39. K. E. Lewis, H. Steiner, J. Chem. Soc. 1964, 3080-3092.
40. P. A. Jacobi, R. W. DeSimone, I. Ghosh, J. Guo, S. H. Leung, D. Pippin, J. Org. Chem. 2000, 65, 8478-8489.
41. E.-i. Negishi, Z. Tan, S.-Y. Liou, B. Liao, Tetrahedron 2000, 56, 10197-10207.