Intramolecular Diels-Alder reactions of trienes tethered with an ether linkage

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 695-724

  Ainsworth, Peter J ^a   Craig, Donald ^a   Reader, John C ^a   Slawin, Alexandra M Z ^a   White, Andrew J P ^a   Williams, David J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; POLYENE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030048161     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00920-5     Document Type: Article

References (56)

1. Craig, D.; Reader, J. C. Tetrahedron Lett. 1990, 31, 6585; Craig, D.; Reader, J. C. Tetrahedron Lett. 1992, 33, 4073, 6165.
2. Craig, D.; Reader, J. C. Tetrahedron Lett. 1990, 31, 6585; Craig, D.; Reader, J. C. Tetrahedron Lett. 1992, 33, 4073, 6165.
3. Ainsworth, P. J.; Craig, D., manuscript in preparation. For examples of other IMDA reactions of trienes tethered with carbon acetals, see: Boeckman, R. K. Jr.; Flann, C. J. Tetrahedron Lett. 1983, 24, 1655; Boeckman, R. K. Jr.; Estep, K. G.; Nelson, S. G.; Walters, M. A. Tetrahedron Lett. 1991, 32, 4095.
4. Ainsworth, P. J.; Craig, D., manuscript in preparation. For examples of other IMDA reactions of trienes tethered with carbon acetals, see: Boeckman, R. K. Jr.; Flann, C. J. Tetrahedron Lett. 1983, 24, 1655; Boeckman, R. K. Jr.; Estep, K. G.; Nelson, S. G.; Walters, M. A. Tetrahedron Lett. 1991, 32, 4095.
5. Ainsworth, P. J.; Craig, D., manuscript in preparation. For examples of other IMDA reactions of trienes tethered with carbon acetals, see: Boeckman, R. K. Jr.; Flann, C. J. Tetrahedron Lett. 1983, 24, 1655; Boeckman, R. K. Jr.; Estep, K. G.; Nelson, S. G.; Walters, M. A. Tetrahedron Lett. 1991, 32, 4095.
6. Craig, D.; Ford, M. J.; Stones, J. A., submitted for publication.
7. Preliminary communication: Craig, D.; Reader, J. C. Synlett 1992, 757. For other examples of IMDA reactions of trienes possessing an ether linkage within the tether, see: Boeckman, R. K. Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789; Burke, S. D.; Smith Strickland, S. M.; Powner, T. H. J. Org. Chem. 1983, 48, 454.
8. Preliminary communication: Craig, D.; Reader, J. C. Synlett 1992, 757. For other examples of IMDA reactions of trienes possessing an ether linkage within the tether, see: Boeckman, R. K. Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789; Burke, S. D.; Smith Strickland, S. M.; Powner, T. H. J. Org. Chem. 1983, 48, 454.
9. Preliminary communication: Craig, D.; Reader, J. C. Synlett 1992, 757. For other examples of IMDA reactions of trienes possessing an ether linkage within the tether, see: Boeckman, R. K. Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789; Burke, S. D.; Smith Strickland, S. M.; Powner, T. H. J. Org. Chem. 1983, 48, 454.
10. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
11. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
12. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
13. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
14. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
15. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
16. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
17. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
18. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
19. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
20. For reviews of the IMDA reaction, see: Carlson, R. G. Ann. Rep. Med. Chem. 1974, 9, 270; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10; Oppolzer, W. Synthesis 1978, 793; Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63; Funk, R.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41; Ciganek, E. Org. React. 1984, 32, 1; Fallis, A. G. Can. J. Chem. 1984, 62, 183; Taber, D. F. Intramolecular Diels-Alder Reactions and Alder Ene Reactions; Springer: Berlin, 1984; Craig, D. Chem. Soc. Rev. 1987, 16, 187; Roush, W. R. In Advances in Cycloaddition, Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, p 91; Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 513.
21. (i) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295;
22. (ii) Chan, T. H.; Fleming, I. Synthesis 1979, 761;
23. (iii) Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745;
24. (iv) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71;
25. (v) Nishiyama, H.; Narimatsu, S.; Sakuta, K.; Itoh, K. J. Chem. Soc., Chem. Commun. 1982, 459
26. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357; Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.
27. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357; Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.
28. Roush, W. R.; Gillis, H. R. J. Org. Chem. 1982, 47, 4825.
29. Craig, D.; Fischer, D. A.; Kemal, Ö.; Marsh, A.; Plessner, T. Tetrahedron 1991, 47, 3095.
30. Culvenor, C. C. J.; Davies, W.; Savige, W. E. J. Chem. Soc. 1949, 2198.
31. Ainsworth, P. J.; Craig, D.; Reader, J. C.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, in press.
32. Hosomi, A.; Saito, M.; Sakurai, H. Tetrahedron Lett. 1980, 21, 3783.
33. Mekhalfia, A.; Markó, I. E. Tetrahedron Lett. 1991, 32, 4779.
34. See the Experimental section for full details of the one-pot reactions.
35. E,E-isomer.
36. E,E-isomer.
37. Z,Z-isomer.
38. 1Z,7E-isomer.
39. [3R,5R]-isomer. [3R,5R]-3,5-Dimethylcyclohexanone was synthesised according to Oppolzer, W.; Petrzilka, M. Helv. Chim. Acta 1978, 61, 2755, and references therein.
40. [2S,5R]-isomer.
41. The triene was formed as a single diastereomer.
42. The triene was formed as a ca. 1.6:1 mixture of diastereomers.
43. We thank Dr Patrick Camilleri and Ms Jeanette Tribe (SmithKline Beecham Pharmaceuticals, The Frythe) for assistance with these separations.
44. For example, see: Ichihara, A.; Kawagishi, H.; Tokugawa, N.; Sakamura, S. Tetrahedron Lett. 1986, 27, 1347.
45. Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
46. 2AlCl-mediated IMDA reactions carried out at room temperature for the times indicated. See Experimental section for details.
47. Paquette and co-workers found that intermolecular Diels-Alder reactions of (phenylsulfonyl)ethene were not accelerated by the addition of Lewis acids, pointing towards the weak Lewis basicity of the sulfonyl oxygen atoms: Carr, R. V. C.; Williams, R. V.; Paquette, L. A. J. Org. Chem. 1983, 48, 4976. However, allylic and tertiary sulfones may be cleaved by oxaphilic Lewis acids: Trost, B. M.; Reza Ghadiri, M. J. Am. Chem. Soc. 1986, 108, 1098, and references therein.
48. Paquette and co-workers found that intermolecular Diels-Alder reactions of (phenylsulfonyl)ethene were not accelerated by the addition of Lewis acids, pointing towards the weak Lewis basicity of the sulfonyl oxygen atoms: Carr, R. V. C.; Williams, R. V.; Paquette, L. A. J. Org. Chem. 1983, 48, 4976. However, allylic and tertiary sulfones may be cleaved by oxaphilic Lewis acids: Trost, B. M.; Reza Ghadiri, M. J. Am. Chem. Soc. 1986, 108, 1098, and references therein.
49. Ganem, B.; Small, V. R. Jr. J. Org. Chem. 1974, 39, 3728.
50. Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249. For regioselective TMSI-mediated cleavage of the tricyclic product of an IMDA reaction of an ether-tethered triene, see: Funk, R. L.; Mossman, C. J.; Zeller, W. E. Tetrahedron Lett. 1984, 25, 1655.
51. Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249. For regioselective TMSI-mediated cleavage of the tricyclic product of an IMDA reaction of an ether-tethered triene, see: Funk, R. L.; Mossman, C. J.; Zeller, W. E. Tetrahedron Lett. 1984, 25, 1655.
52. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd edn.; Pergamon: Oxford, 1988.
53. Prepared analogously to methyl (E)-4-hydroxy-2-butenoate: see reference 11.
54. Holton, R. A.; Kim, H.-B. Tetrahedron Lett. 1986, 27, 2191.
55. Atomic coordinates are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW. Any request should be accompanied by the full literature citation for this work.
56. The SHELXTL-PC Programme System (Version 4.2) was used: Sheldrick, G. M.; Siemens Analytical X-Ray Instruments, Madison, Wisconsin, 1992.