An approach to the cephalotaxine ring skeleton using an ammonium Ylide/Stevens [1,2]-rearrangement

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4159-4162

  Beall, L Scott ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMMONIA; BENZAZEPINE DERIVATIVE; CEPHALOTAXINE; COPPER; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

CEPHALOTAXUS;

EID: 0032508006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00774-6     Document Type: Article

References (39)

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30. 17. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Chem. Rev. 1986, 86, 919. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p 387. Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, p 1045.
31. 17. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Chem. Rev. 1986, 86, 919. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p 387. Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, p 1045.
32. 17. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Chem. Rev. 1986, 86, 919. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p 387. Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, p 1045.
33. 17. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Chem. Rev. 1986, 86, 919. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p 387. Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, p 1045.
34. 17. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Chem. Rev. 1986, 86, 919. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p 387. Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, p 1045.
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36. 19. For reports regarding the superiority of copper catalysts for generation of onium ylides, see: West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.
37. 19. For reports regarding the superiority of copper catalysts for generation of onium ylides, see: West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.
38. 20. Both compounds 24 and 25 consisted of a 1:1-mixture of diastereomers.
39. 21. For a similar reaction in the 6,6-system, see: Zaragoza, F. Synlett 1995, 237.