o-quinone methides from 4-allenylcyclobutenones: Synthesis and chemistry

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 329-340

  Taing, Meng ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000750712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951445m     Document Type: Article

References (59)

1. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
2. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
3. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
4. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
5. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
6. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
7. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
8. For lead references concerning the synthesis of substituted cyclobutenones, see: Schmidt, A. H.; Ried, W. Synthesis 1978, 1. Knorr, H.; Ried, W. Synthesis 1978, 649. Schmidt, A. H.; Ried, W. Synthesis 1978, 869. Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. Liebeskind, L. S.; Wirtz, K. R. J. Org. Chem. 1990, 55, 5350. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 4293.
9. Excellent reviews of allene chemistry are the following: Moreau, J. L. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed ; Wiley: New York, 1980; p 363. Schuster, H. E.; Coppola, G. M. Allenes In Organic Synthesis; Wiley: New York, 1984. For a specific reference to 1-lithio-1-methoxyallene, see: Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916. Weiberth, F J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
10. Excellent reviews of allene chemistry are the following: Moreau, J. L. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed ; Wiley: New York, 1980; p 363. Schuster, H. E.; Coppola, G. M. Allenes In Organic Synthesis; Wiley: New York, 1984. For a specific reference to 1-lithio-1-methoxyallene, see: Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916. Weiberth, F J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
11. Excellent reviews of allene chemistry are the following: Moreau, J. L. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed ; Wiley: New York, 1980; p 363. Schuster, H. E.; Coppola, G. M. Allenes In Organic Synthesis; Wiley: New York, 1984. For a specific reference to 1-lithio-1-methoxyallene, see: Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916. Weiberth, F J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
12. Excellent reviews of allene chemistry are the following: Moreau, J. L. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed ; Wiley: New York, 1980; p 363. Schuster, H. E.; Coppola, G. M. Allenes In Organic Synthesis; Wiley: New York, 1984. For a specific reference to 1-lithio-1-methoxyallene, see: Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916. Weiberth, F J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
13. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
14. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
15. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
16. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
17. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
18. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
19. For reviews on the chemistry of quinone methides, see: Veciana, J.; Martinez, A. D.; Armet, O. Rev. Chem. Intermed. 1988, 10 (1), 35-70. Volod'kin, A. A.; Ershov, V. V. Usp. Khim. 1988, 57 (4), 595-624 . Also see the following and references cited therein; Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1990, 55, 3708-10. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698-700. Angle, S. R.; Yang, W. J. Am. Chem. Soc. 1990, 112, 4524-8. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193-6. Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136-8.
20. Allenes in this series are conveniently prepared from readily available propargyl ethers. See for examples: Corey, E. J.; Terashim, S. Tetrahedron Lett. 1972, 1819. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593.
21. Allenes in this series are conveniently prepared from readily available propargyl ethers. See for examples: Corey, E. J.; Terashim, S. Tetrahedron Lett. 1972, 1819. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593.
22. Allenes in this series are conveniently prepared from readily available propargyl ethers. See for examples: Corey, E. J.; Terashim, S. Tetrahedron Lett. 1972, 1819. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593.
23. For a recent detailed reviews on related ring expansions of cyclobutenones, see: Moore, H. W.; Yerxa, B. R. Chemtracts: Org. Chem. 1992, 5, 273. Moore, H. W.; Yerxa, B. R. Advances in Strain in Organic Chemistry; JAI: London, 1995; Vol. 4.
24. For a recent detailed reviews on related ring expansions of cyclobutenones, see: Moore, H. W.; Yerxa, B. R. Chemtracts: Org. Chem. 1992, 5, 273. Moore, H. W.; Yerxa, B. R. Advances in Strain in Organic Chemistry; JAI: London, 1995; Vol. 4.
25. For reviews on the synthetic utility of vinylsilanes, see: Fleming, I. Kem. Kemi 1982, 9(5), 365. Huang, Z. Huaxue Shiji 1991, 13 (1), 32. Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
26. For reviews on the synthetic utility of vinylsilanes, see: Fleming, I. Kem. Kemi 1982, 9(5), 365. Huang, Z. Huaxue Shiji 1991, 13 (1), 32. Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
27. For reviews on the synthetic utility of vinylsilanes, see: Fleming, I. Kem. Kemi 1982, 9(5), 365. Huang, Z. Huaxue Shiji 1991, 13 (1), 32. Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
28. The authors have deposited atomic coordinates for compound 3a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
29. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
30. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
31. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
32. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
33. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
34. For examples of 1,5-hydrogen shift involving o-quinone methides, see: Yamashita, A.; Toy, A.; Scahill, T. A. J. Org. Chem. 1989, 54, 3625. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 1159. Arduni, A.; Pochini, A ; Ungaro, R. Synthesis 1984, 950. Jurd, D. Aust. J. Chem. 1978, 31, 347. Casnati, G.; Pochini, A.; Terenghi, G. M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783.
35. Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press Inc.: London, 1987; pp 193-199.
36. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076. Bassindale, A. R.; Brook, A. G.; Jones, P. F.; Lennon, J. M. Can. J. Chem. 1975, 53, 332. Reetz, M. T.; Greif, N. Angew. Chem., Int. Ed. Engl. 1977, 16, 712 Tacke, R.; Lange, H. Chem. Ber. 1983, 116, 3585.
37. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076. Bassindale, A. R.; Brook, A. G.; Jones, P. F.; Lennon, J. M. Can. J. Chem. 1975, 53, 332. Reetz, M. T.; Greif, N. Angew. Chem., Int. Ed. Engl. 1977, 16, 712 Tacke, R.; Lange, H. Chem. Ber. 1983, 116, 3585.
38. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076. Bassindale, A. R.; Brook, A. G.; Jones, P. F.; Lennon, J. M. Can. J. Chem. 1975, 53, 332. Reetz, M. T.; Greif, N. Angew. Chem., Int. Ed. Engl. 1977, 16, 712 Tacke, R.; Lange, H. Chem. Ber. 1983, 116, 3585.
39. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076. Bassindale, A. R.; Brook, A. G.; Jones, P. F.; Lennon, J. M. Can. J. Chem. 1975, 53, 332. Reetz, M. T.; Greif, N. Angew. Chem., Int. Ed. Engl. 1977, 16, 712 Tacke, R.; Lange, H. Chem. Ber. 1983, 116, 3585.
40. Makriyannis, A; Rapaka, R. S. Life Sci. 1990, 47, 2173.
41. (a) Cannabinoids as Therapeutic Agents; Mechoulam, R., Ed.; CRC Press, Inc.: Boca Raton, FL, 1986.
42. (b) Little, P. J.; Compton, D. R.; Johnson, M. R.; Melvin, L. S.; Martin, B. R. J. Pharmacol. Exp. Ther. 1988, 247, 1046.
43. (c) Feigenbaum, J J.; Richmond, S. A.; Weissman, Y.; Mechoulam, R. Eur. J. Pharmacol. 1989, 169, 159.
44. (d) Tius, M. A.; Busch-Petersen, J. Tetrahedron Lett. 1994, 35, 5181.
45. (e) Tius, M. A.; Kannangara, G. S. K. J. Org. Chem. 1990, 55, 5711.
46. (f) Yan, G.; Yan, G.; Yin, D.; Khanolka, A. D.; Compton, D. R.; Martin, B. R.; Makriyannis, A. J. Med. Chem. 1994, 37, 2619.
47. Mechoulam, R.; Lander, N.; Varkony, T. H.; Kimmel, I.; Becker, O.; Ben-Zri, Z. J. Med Chem. 1980, 23, 1068.
48. Marino, J. P.; Dax, S. L. J. Org. Chem. 1984, 49, 3671.
49. For a related synthesis of hexahydroeannabanol itself, see: Tietze, L.-F.; Kiedrowski, G.; Harms, K.; Clegg, W.; Sheldrick, G. Angew. Chem., Int. Ed Engl. 1980, 19, 134. Archer, R. A.; Boyd, D. B.; Demarco, P. V.; Tyminski, I. J.; Allinger, N. L. J. Am. Chem. Soc. 1990, 92, 5200.
50. For a related synthesis of hexahydroeannabanol itself, see: Tietze, L.-F.; Kiedrowski, G.; Harms, K.; Clegg, W.; Sheldrick, G. Angew. Chem., Int. Ed Engl. 1980, 19, 134. Archer, R. A.; Boyd, D. B.; Demarco, P. V.; Tyminski, I. J.; Allinger, N. L. J. Am. Chem. Soc. 1990, 92, 5200.
51. A values were taken from the following reference: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley and Sons, Inc: New York, 1994.
52. Kirmse, W.; Rondam, N. G.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 975. Niwayama, S.; Kallel, E. A.; Houk, K. N. J. Org. Chem., in press.
53. Kirmse, W.; Rondam, N. G.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 975. Niwayama, S.; Kallel, E. A.; Houk, K. N. J. Org. Chem., in press.
54. (a) Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593.
55. (b) Mantione, R.; Leroux, Y. J. Organomet. Chem 1971, 31, 15.
56. (a) Ruitenberg, K.; Westmijze, H.; Kleijn, H.; Vermeer, P. J. Organomet. Chem. 1984, 277, 227.
57. (b) Lequan, M.; Guillerm, G. J. Organomet. Chem. 1973, 54, 153.
58. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis (Best Synthetic Methods); Academic Press: San Diego, 1988.
59. (b) Rajagopalan, S.; Zweifel, G. Synthesis 1984, 1120.