The vinylogous aldol addition of heterocyclic silyloxy dienes: Application in synthesis

Synlett

Volumn , Issue 9, 1999, Pages 1333-1350

  Rassu, G ^a   Zanardi, F ^b   Battistini, L ^b   Casiraghi, G ^b  

^a Ist per l'Applic delle Tecniche C   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Diastereoselective synthesis; Heterocyclic compounds; Silyloxy dienes; Vinylogous aldol addition

Indexed keywords

ALDEHYDE DERIVATIVE; ALKADIENE; HETEROCYCLIC COMPOUND; IMINE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032875333     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2832     Document Type: Article

References (90)

1. Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon: Oxford, 1991; Voll. 1-8. Nicolau, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1996.
2. Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon: Oxford, 1991; Voll. 1-8. Nicolau, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1996.
3. See, for example: Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Hanessian, S. Aldrichimica Acta 1989, 22, 3. Sharpless, K. B. Tetrahedron 1994, 50, 4235. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
4. See, for example: Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Hanessian, S. Aldrichimica Acta 1989, 22, 3. Sharpless, K. B. Tetrahedron 1994, 50, 4235. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
5. See, for example: Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Hanessian, S. Aldrichimica Acta 1989, 22, 3. Sharpless, K. B. Tetrahedron 1994, 50, 4235. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
6. See, for example: Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Hanessian, S. Aldrichimica Acta 1989, 22, 3. Sharpless, K. B. Tetrahedron 1994, 50, 4235. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
7. See, for example: Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. Hanessian, S. Aldrichimica Acta 1989, 22, 3. Sharpless, K. B. Tetrahedron 1994, 50, 4235. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
8. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier; Amsterdam, 1992; Vol. 11, p 429. Casiraghi, G.; Rassu, G. Synthesis 1995, 607. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Casiraghi, G.; Rassu, G.; Zanardi, F. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, 1998; Chapter 17, p 327. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1998; Vol. 3, p 113.
9. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier; Amsterdam, 1992; Vol. 11, p 429. Casiraghi, G.; Rassu, G. Synthesis 1995, 607. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Casiraghi, G.; Rassu, G.; Zanardi, F. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, 1998; Chapter 17, p 327. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1998; Vol. 3, p 113.
10. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier; Amsterdam, 1992; Vol. 11, p 429. Casiraghi, G.; Rassu, G. Synthesis 1995, 607. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Casiraghi, G.; Rassu, G.; Zanardi, F. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, 1998; Chapter 17, p 327. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1998; Vol. 3, p 113.
11. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier; Amsterdam, 1992; Vol. 11, p 429. Casiraghi, G.; Rassu, G. Synthesis 1995, 607. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Casiraghi, G.; Rassu, G.; Zanardi, F. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, 1998; Chapter 17, p 327. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1998; Vol. 3, p 113.
12. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier; Amsterdam, 1992; Vol. 11, p 429. Casiraghi, G.; Rassu, G. Synthesis 1995, 607. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Casiraghi, G.; Rassu, G.; Zanardi, F. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, 1998; Chapter 17, p 327. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1998; Vol. 3, p 113.
13. Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 157.
14. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5. Braun, M. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry), Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E 21b, p 1603. Casiraghi, G., Rassu, G., Zanardi, F. In Seminars in Organic Synthesis, Società Chimica Italiana, Ed.; Editor: Milano, 1996; p 211.
15. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5. Braun, M. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry), Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E 21b, p 1603. Casiraghi, G., Rassu, G., Zanardi, F. In Seminars in Organic Synthesis, Società Chimica Italiana, Ed.; Editor: Milano, 1996; p 211.
16. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5. Braun, M. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry), Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E 21b, p 1603. Casiraghi, G., Rassu, G., Zanardi, F. In Seminars in Organic Synthesis, Società Chimica Italiana, Ed.; Editor: Milano, 1996; p 211.
17. n) according to the distance between the key functional group and the actual reactive carbon atom. Fuhrhop, J., Penzlin, G. In Organic Synthesis, VCH: Weinheim, New York, 1994; pp 1-17.
18. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
19. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
20. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
21. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
22. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
23. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
24. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
25. Pioneering works: Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893. Kabas, G. Tetrahedron 1966, 22, 1213. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319. Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161. Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467.
26. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
27. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
28. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
29. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
30. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
31. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
32. Recent applications: Paterson, I., Smith, J. D. J. Org. Chem. 1992, 57, 3261. Mulzer, J., Dupré, S., Buschmann, J., Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452. Hara, R., Furukawa, T., Horiguchi, Y., Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186. Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552. Krüger, J., Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. Cahard, D., Poirier, J.-M., Duhamel, P. Tetrahedron Lett. 1998, 39, 7093. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
33. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
34. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
35. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
36. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
37. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
38. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
39. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
40. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
41. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
42. For related vinylogous Mannich reactions see, for example: Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913, Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613. Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G. Synth. Commun. 1992, 22, 2305. Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293. Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236. See also: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
43. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
44. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
45. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
46. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
47. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
48. When we started with our program, it was surprising to discover that exploitation of synthons of type 20 had only been described for few 2-(trimethylsilyloxy)furan adducts in connection with the synthesis of polyene compounds, squandering almost all the valuable functionaliy and diverse chemical reactivity present in that matrices. For work in this field see, for example: Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101. von der Ohe, F.; Brückner, R. Tetrahedron Lett. 1998, 39, 1909. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707, and references therein.
49. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
50. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
51. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
52. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
53. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
54. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
55. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
56. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
57. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
58. Pioneering works: Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663. Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269. Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M.; Dembech, P. J. Org. Chem. 1984, 49, 551. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037. Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-A. Tetrahedron Lett. 1987, 28, 985. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
59. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 2135.
60. Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025.
61. Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron; Asymmetry 1997, 8, 3237.
62. Spanu, P.; Rassu, G.; Ulgheri, F.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron 1996, 52, 4829.
63. Knapp, S. Chem. Rev. 1995, 95, 1859.
64. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 6523.
65. Soro, P.; Rassu, G.; Pinna, L.; Zanardi, F.; Casiraghi, G. J. Org. Chem. 1996, 61, 5172.
66. Casiraghi, G.; Zanardi, F.; Rassu, G.; Pinna, L. Org. Prep. Proced. Int. 1996, 28, 641.
67. Casiraghi, G.; Spanu, P.; Rassu, G.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1994, 59, 2906.
68. Casiraghi, G.; Ulgheri F.; Spanu, P.; Rassu, G.; Pinna, L.; Gasparri Fava, G.; Belicchi Ferrari, M.; Pelosi, G. J. Chem. Soc. Perkin Trans. 1 1993, 2991.
69. Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513.
70. Pichon, M.; Jullian, J.-C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1998, 39, 1755. Szlosek, M.; Franck, X.; Figadère, B.; Cavé, A. J. Org. Chem. 1998, 63, 5169. See also: Baussanne, I.; Schwardt, O.; Royer, J., Pichon, M.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1997, 38, 2259.
71. Pichon, M.; Jullian, J.-C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1998, 39, 1755. Szlosek, M.; Franck, X.; Figadère, B.; Cavé, A. J. Org. Chem. 1998, 63, 5169. See also: Baussanne, I.; Schwardt, O.; Royer, J., Pichon, M.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1997, 38, 2259.
72. Pichon, M.; Jullian, J.-C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1998, 39, 1755. Szlosek, M.; Franck, X.; Figadère, B.; Cavé, A. J. Org. Chem. 1998, 63, 5169. See also: Baussanne, I.; Schwardt, O.; Royer, J., Pichon, M.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1997, 38, 2259.
73. Rassu, G.; Zanardi, F.; Battistini, L.; Gaetani, E.; Casiraghi, G. J. Med. Chem. 1997, 40, 168.
74. Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G.; Gasparri Fava, G.; Ferrari Belicchi, M.; Pelosi G. Tetrahedron 1992, 48, 727.
75. Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Gasparri Fava, G.; Belicchi Ferrari, M.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
76. Rassu, G.; Carta, P.; Pinna, L.; Battistini, L. Presented at the 12th International Conference on Organic Synthesis, Venezia, June 28 -July 2 1998, book of abstracts p 357.
77. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397.
78. Battistini, L.; Zanardi, F., Rassu, G.; Casiraghi, G., unpublished results from this laboratory.
79. With α-alkoxy imines, two Felkin-type models likely operate (I and II in Scheme 24). When a bulky R-group is involved, model II is favored (see reaction 22+108 → 109 in Scheme 23), whereas model I prevails with less demanding R-substituents (see reaction 22+103 → 104 in Scheme 22).
80. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371.
81. 4 guidance: Jégou, A.; Veyrières, A. Tetrahedron: Asymmetry 1998, 9, 3129. Veyrières, A. Presented at GECO XXXIX Groupe dnEtudes de Chimie Organique, La Bourbole, 30 Août-4 Septembre 1998, book of abstracts.
82. 4 guidance: Jégou, A.; Veyrières, A. Tetrahedron: Asymmetry 1998, 9, 3129. Veyrières, A. Presented at GECO XXXIX Groupe dnEtudes de Chimie Organique, La Bourbole, 30 Août-4 Septembre 1998, book of abstracts.
83. Rassu, G.; Carta, P.; Pinna, L.; Battistini, L.; Zanardi, F.; Acquotti, D.; Casiraghi, G. Eur. J. Org. Chem., in press.
84. Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299.
85. For a preparatory work, see: Zanardi, F.; Battistini, L.; Rassu, G.; Pinna, L.; Mor, M.; Culeddu, N.; Casiraghi, G. J. Org. Chem. 1998, 63, 1368.
86. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Hertz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol 70, p 81. For a review dealing with the chemical synthesis of annonaceous acetogenins and related structures see, for example: Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. ChemTracts-Org. Chem. 1998, 11, 803.
87. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Hertz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol 70, p 81. For a review dealing with the chemical synthesis of annonaceous acetogenins and related structures see, for example: Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. ChemTracts-Org. Chem. 1998, 11, 803.
88. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Hertz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol 70, p 81. For a review dealing with the chemical synthesis of annonaceous acetogenins and related structures see, for example: Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. ChemTracts-Org. Chem. 1998, 11, 803.
89. A strictly related reiterative approach to a series of oligotetrahydrofuranic motifs related to the annonaceous acetogenins has been independently introduced by B. Figadère and co-workers using 2-(trimethylsilyloxy)furan (22): Figadère, B.; Peyrat, J.-F.; Cavé, A. J. Org. Chem. 1997, 62, 3428.
90. Battistini, L.; Pinna, L.; Rassu, G.; Zanardi, F.; Casiraghi, G., unpublished results.