Intramolecular Diels-Alder reactions of carbon acetal-tethered trienes

Tetrahedron

Volumn 52, Issue 26, 1996, Pages 8937-8946

  Ainsworth, Peter J ^a   Craig, Donald ^a   White, Andrew J P ^a   Williams, David J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; POLYENE;

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

EID: 0029895330     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00442-5     Document Type: Article

References (23)

1. Ainsworth, P. J.; Craig, D.; Reader, J. C.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 11601.
2. Ainsworth, P. J.; Craig, D.; Reader, J. C.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 695.
3. Craig, D.; Ford, M. J.; Stones, J. A. Tetrahedron Lett. 1996, 37, 535.
4. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
5. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
6. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
7. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
8. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
9. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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.
10. For recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 recent other work on tethered Diels-Alder reactions, see: Shea, K. J.; Gauthier, D. R. Tetrahedron Lett. 1994, 35, 7311. 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 previous examples of 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.
17. For previous examples of 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.
18. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
19. Mukaiyama, T.; Ohshima, M.; Murakami, M. Chem. Lett. 1984, 265.
20. Prepared from ethoxycarbonylethylidenetriphenylphosphorane and glycolaldehyde dimer analogously to the method used for the methyl ester described in reference 1.
21. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd edn.; Pergamon: Oxford, 1988.
22. 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.
23. SHELXTL PC Release 4.1, May 1990; Siemens Analytical X-Ray Instruments, Inc., Madison, Wisconsin.