Dual behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions. Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9156-9167

  Hsu, Po Yi ^a   Peddinti, Rama Krishna ^a   Chittimalla, Santhosh Kumar ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ELECTRON ENERGY LEVELS; MOLECULAR STRUCTURE; OXIDATION; SUBSTITUTION REACTIONS;

DIELS-ALDER REACTION; DIENOLS; O-BENZOQUINONES; STEREOSELECTIVITY;

PHENOLS;

3 (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 3 METHOXY 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 3 METHOXY 6,8 DIMETHYL 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 3 METHOXY 8 METHYL 10 (1 PROPENYL) 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 3 METHOXY 8 METHYL 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 5 ETHYL 5A METHYL 8A METHOXY 8 OXO 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 5,5A DICARBOXYLATE; 5A (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; 5A (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 8A METHOXY 2A METHYL 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; 5A (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 8A METHOXY 5 METHYL 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; 8 (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 3 METHOXY 10 (1 PROPENYL) 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 8 (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 3 METHOXY 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 8 (5,5 DIMETHYL 1,3 DIOXAN 2 YL) 3 METHOXY 6 METHYL 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 ONE; 8A METHOXY 2A,5A DIMETHYL 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; 8A METHOXY 5,5A DIMETHYL 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; 8A METHOXY 5A METHYL 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 8 ONE; ALKADIENE; BENZOQUINONE DERIVATIVE; DECALIN; ETHYL 3 [6 METHOXY 8 (METHOXYCARBONYL) 10 OXO 5 OXATRICYCLO[4.3.1.0 3,7]DEC 8 EN 2 YL] 2 PROPENOATE; GUAIACOL; METHYL 3 METHOXY 2 OXO 10 (1 PROPENYL) 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 ENE 8 CARBOXYLATE; METHYL 3 METHOXY 2 OXO 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 ENE 8 CARBOXYLATE; METHYL 3 METHOXY 6 METHYL 2 OXO 10 ETHENYL 4 OXATRICYCLO[4.3.1.0 3,7]DEC 8 ENE 8 CARBOXYLATE; METHYL 8A METHOXY 2A METHYL 8 OXO 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 5A CARBOXYLATE; METHYL 8A METHOXY 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 5A CARBOXYLATE; METHYL 8A METHOXY 5 METHYL 8 OXO 2A,5,5A,8,8A,8B HEXAHYDRO 2H BENZO[CD]ISOBENZOFURAN 5A CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; COPE REARRANGEMENT; DIELS ALDER REACTION; ELECTRON TRANSPORT; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 27744545386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0510179     Document Type: Article

References (54)

1. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
2. (a) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction: Selected Practical Methods; Wiley: Chichester, 2002.
3. (b) Fãllis, A. G.; Lu, Y.-F. Advances in Cycloadditions; JAI Press, Inc.: Greenwich, CT, 1993; Vol. 3, Chapter 1, pp 1-66.
4. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 4.1, pp 316-399.
5. (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
6. (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. E. Angew. Chem., Int. Ed. 2002, 41, 1668.
7. (c) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078.
8. (a) Trost, B. M. Science 1991, 254, 1471.
9. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
10. (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B., Ed.; Oxford: Pergamon Press, 1991; Vol. 5, pp 513-550.
11. (b) Fallis, A. G. Acc. Chem. Res. 1999, 32, 464.
12. (c) Brocksom, T. J.; Nakamura, J.; Ferreira, M. L.; Brocksom, U. J. Braz. Chem. Soc. 2001, 12, 597.
13. (d) Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem., Int. Ed. 2001, 40, 820.
14. (e) Anderson, J. C.; Blake, A. J.; Graham, J. P.; Wilson, C. Org. Biomol. Chem. 2003, 16, 2877.
15. (a) Kirby, A. J. Adv. Phy. Org. Chem. 1980, 17, 183.
16. (b) Page, M. I. Chem. Soc. Rev. 1973, 2, 295.
17. (a) Neuschutz, K.; Velker, J.; Neier, R. Synthesis 1998, 227.
18. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167.
19. (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
20. (b) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
21. (c) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
22. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
23. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
24. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
25. (a) Liao, C.-C. In Modern Methodology in Organic Synthesis; Sheno, T., Ed.; Kodansha: Tokyo, 1992; pp 409-424.
26. (b) Quideau, S.; Pouységu, L. Org. Prep. Proc. Int. 1999, 31, 617.
27. (c) Liao, C.-C., Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856.
28. (d) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383.
29. (a) Andersson, G.; Berntsson, P. Acta Chem. Scand. B 1975, 29, 948.
30. (b) Yen, C.-F.; Peddinti, R. K.; Liao, C.-C. Org. Lett. 2002, 2, 2909.
31. (a) Liao, C.-C.; Chu, C.-S.; Lee, T.-H.; Rao, P. D.; Ko, S.; Song, L.-D.; Hsiao, H.-C. J. Org. Chem., 1999, 64, 4102.
32. (b) Lai, C.-H.; Shen, Y.-L.; Wang, M.-N.; Rao, N. S. K.; Liao, C.-C. J. Org. Chem. 2002, 67, 6493.
33. (a) Tamura, Y.; Yakura, T.; Harnata, J. I.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
34. (b) Yahura, T.; Tohma, H.; Kikchi, K.; Kita, Y. Synthesis 1989, 126.
35. (c) Sutherland, H. S.; Higgs, K. C.; Taylor, N. J.; Rodrigo, R. Tetrahedron 2001, 57, 309.
36. Hwang, J.-T., Liao, C.-C. Tetrahedron Lett. 1991, 32, 6583.
37. (a) Chu, C.-S.; Lee, T.-H.; Rao, P. D.; Song, L.-D.; Liao, C.-C. J. Org. Chem. 1999, 64, 4111.
38. (b) Lin, K.-C.; Shen, Y.-L.; Rao, N. S. K.; Liao, C.-C. J. Org. Chem. 2002, 67, 8157.
39. (a) Chen, C.-H.; Rao, P. D.; Liao, C.-C. Chem. Commun. 1998, 155.
40. (b) Chen, C.-H.; Peddinti, R. K.; Rao, N. S. K.; Liao, C.-C. J. Org. Chem. 2004, 69, 5365.
41. Hsu, P.-Y.; Liao, C.-C. Chem. Commun. 1997, 1085.
42. (a) Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. Chem. Commun. 1998, 1085.
43. (b) Carlini, R.; Higgs, K.; Older, C.; Randhawa, S.; Rodrigo, R. J. Org. Chem. 1997, 62, 2330.
44. Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889.
45. Deslongchamps, P.; Beruhe, G. Can. J. Chem. 1990, 68, 404.
46. House, H. U.; Rasmussun, G. H. J. Org. Chem. 1961, 26, 4278.
47. (a) Kato, N.; Kataoka, H.; Ohbuchi, S.; Tanaka, S.; Takashita, H. J. Chem. Soc., Chem. Commun. 1988, 354.
48. (b) Shea, K. J.; Philips, R. B. J. Am. Chem. Soc. 1980, 102, 3156.
49. (c) Shea, K. J.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1499.
50. Brown, J. M.; Golding, B. T.; Stofko, J. J., Jr. J. Chem. Soc., Chem. Commun. 1973, 319.
51. (a) Tamaru, Y.; Harada, T.; Yoshida, Z. J. Am. Chem. Soc. 1980, 102, 2392.
52. (b) Zieglar, F. E.; Piwinski, J. J. J. Am. Chem. Soc. 1979, 101, 1611.
53. (c) Conia, J. M.; Sandre-Le, C. A. Tetrahedron Lett. 1962, 505.
54. (d) Cope, A. C.; Hoyle, K. E.; Heyl, D. J. Am. Chem. Soc. 1941, 63, 1843.