Thallium(III)-mediated ring contraction of cis-octalins: An approach for the diastereoselective construction of the nor-bakkane skeleton

Synthesis

Volumn , Issue 16, 2006, Pages 2748-2752

  Ferraz, Helena M C ^a   Vieira, Tiago O ^a   Silva Jr , Luiz F ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Bakkanes; Hydrindanes; Oxidative rearrangement; Ring contraction; Thallium(III)

Indexed keywords

OXIDATION; STEREOCHEMISTRY; THALLIUM COMPOUNDS;

BAKKANES; HYDRINDANES; OXIDATIVE REARRANGEMENT; RING CONTRACTION;

PARAFFINS;

ALKENE; BAKKANE DERIVATIVE; ESTER DERIVATIVE; HYDRINDANE DERIVATIVE; INDAN DERIVATIVE; LACTONE DERIVATIVE; NATURAL PRODUCT; NITRIC ACID DERIVATIVE; THALLIUM; THALLIUM TRINITRATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33748286699     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942500     Document Type: Article

References (50)

1. (a) Abe, N.; Onoda, R.; Shirahata, K.; Kalo, T.; Woods, M. C.; Kitahara, Y. Tetrahedron Lett. 1968, 369.
2. (b) Naya, K.; Takagi, I.; Hayashi, M.; Nakamura, S.; Kobayashi, M.; Katsumura, S. Chem. Ind. (London) 1968, 318.
3. For a review concerning the chemistry of bakkanes, see: Silva, L. F. Jr. Synthesis 2001, 671.
4. For examples, see: (a) Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713.
5. (b) Kano, K.; Hayashi, K.; Mitsuhashi, H. Chem. Pharm. Bull. 1982, 30, 1198.
6. (c) Wu, T.-S.; Kao, M-S.; Wu, P.-L.; Lin, F.-W.; Shi, L.-S.; Liou, M-J.; Li, C.-Y. Chem. Pharm. Bull. 1999, 47, 375.
7. For examples, see: (a) Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotný, L. J. Appl. Entomol. 1984, 98, 394.
8. (b) Nawrot, J.; Harmatha, J.; Novotn, L. Biochem. Syst. Ecol. 1984, 12, 99.
9. Wu, T.-S.; Kao, M-S.; Wu, P.-L.; Lin, F.-W.; Shi, L.-S.; Teng, C.-M. Phytochemistry 1999, 52, 901.
10. Liao, C.-H.; Ko, F.-N.; Wu, T.-S.; Teng, C.-M. J. Pharm. Pharmacol. 1997, 49, 1248.
11. Reddy, D. S. Org. Lett. 2004, 6, 3345.
12. (a) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361.
13. (b) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663.
14. (a) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, (viii), 9.
15. (b) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069.
16. (c) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806.
17. Mori, K.; Matsushima, Y. Synthesis 1995, 845.
18. (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 4691.
19. (b) Evans, D. A.; Sims, C. L.; Andrews, G. C. J. Am. Chem. Soc. 1977, 99, 5453.
20. For some leading references, see: (a) Brocksom, T. J.; Coelho, F.; Depres, J. P.; Greene, A. E.; de Lima, M. E. F.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. Y. J. Am Chem. Soc. 2002, 124, 15313.
21. (b) Hamelin, O.; Wang, Y.; Depres, J. P.; Greene, A. E. Angew. Chem. Int. Ed. 2000, 39, 4314.
22. (c) Hamelin, O.; Deprés, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992.
23. (d) Greene, A. E.; Deprés, J.-P.; Coelho, F.; Brocksom, T. J. J. Org. Chem. 1985, 50, 3943.
24. (e) For other papers, see, for example: ref. 2 and ref. 12a.
25. Kabbe, H.-J. Justus Liebigs Ann. Chem. 1962, 656, 204.
26. (a) Lee, J. B.; Price, M. J. Tetrahedron Lett. 1962, 1155.
27. (b) Lee, J. B.; Price, M. J. Tetrahedron 1964, 20, 1017.
28. Anderson, C. B.; Winstein, S. J. Org. Chem. 1963, 28, 605.
29. For some reviews concerning thallium(III), see: (a) McKillop, A.; Taylor, E. C. In Comprehensive Organometallic Chemistry, Vol. 7; Wilkinson, G., Ed.; Pergamon Press: New York, 1982, 465.
30. (b) Ferraz, H. M. C.; Silva, L. F. Jr.; Vieira, T. de O. Synthesis 1999, 2001.
31. (c) McKillop, A.; Taylor, E. C. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J.; De Jonge, C. R. H. I., Eds.; Plenum: New York, 1986, 695.
32. (a) For a review concerning thallium(III)-mediated ring-contraction reactions, see: Ferraz, H. M, C.; Silva, L. F. Jr. Quim. Nova 2000, 23, 216.
33. (b) For a review concerning ring contraction reactions, see: Silva, L. F. Jr. Tetrahedron 2002, 58, 9137.
34. Ferraz, H. M. C.; Silva, L. F. Jr. Tetrahedron 2001, 57, 9939.
35. Ferraz, H. M. C.; Silva, L. F. Jr.; Vieira, T. O. Tetrahedron 2001, 57, 1709.
36. Silva, L. F. Jr.; Sousa, R. M. F.; Ferraz, H. M. C.; Aguilar, A. M. J. Braz. Chem. Soc. 2005, 16, 1160.
37. (a) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F. Jr. Synthesis 2003, 1031.
38. (b) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F. Jr. Tetrahedron 2003, 59, 5817.
39. Ferraz, H. M. C.; Silva, L. F. Jr. J. Org. Chem. 1998, 63, 1716.
40. Ferraz, H. M. C.; Silva, L. F. Jr. J. Braz. Chem. Soc. 2001, 12, 548.
41. 2-Methylcyclohex-2-enone was prepared in two steps (bromination followed by dehydrohalogenation) from 2-methylcyclohexanone, in 68% yield: Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888.
42. Nagakura, I.; Ogata, H.; Ueno, M.; Kitahara, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2995.
43. Fringuelli, F.; Pizzo, F.; Taticchi, A.; Halls, T. D. J.; Wenkert, E. J. Org. Chem. 1982, 47, 5056.
44. Angell, E. C.; Fringuelli, F.; Pizzo, F.; Taticchi, A.; Wenkert, E. J. Org. Chem. 1988, 53, 1224.
45. McKillop, A.; Hunt, J. D.; Kienzle, F.; Bigham, E.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3635.
46. Abley, P.; Byrd, J. E.; Halpern, J. J. Am. Chem. Soc. 1973, 95, 2591.
47. Sekizaki, H.; Ito, M.; Inoue, S. Bull. Chem. Soc. Jpn. 1978, 51, 2439.
48. Heathcock, C. H.; Ratcliffe, R.; Van, J. J. Org. Chem. 1972, 37, 1796.
49. Ratcliffe, B. E.; Heathcock, C. H. J. Org. Chem. 1972, 37, 531.
50. The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 605577.