Decarbonylation of α-tertiary amino acids. Application to the synthesis of polyhydroxylated indolizidines

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5581-5584

  Rodríguez, Rosa ^a   Bermejo, Francisco ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605851     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01130-6     Document Type: Article

References (22)

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9. 5. Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem., 1996, 61, 314-323.
10. 6. Martín-López, M. J.; Bermejo-González, F. Tetrahedron Lett., 1994, 35, 4235-4238.
11. 7. Martín-López, M. J.; Bermejo-González, F. Tetrahedron Lett., 1994, 35, 8843-8846.
12. 3N, tol, 90 °C) carried out on the carboxy oxazolidinone 9. In this case, the regioselectivity of the process is governed by the acidity of the benzylic proton to yield 11 in 85% yield; F. Bermejo and R. Rodríguez, unpublished results. (equation presented)
13. 9. For recent reviews on the chemistry and biology of polyhidroxyindolizidine alkaloids, see: Elbein, A. D.; Molyneux, R. J., Alkaloids: Chemical and Biological perspectives; Pelletier, S. W.; Ed.; Wiley; New York, 1987; vol. 5, chapter 1, pp. 1-54. Howard, A. S.; Michael, J. P. Alkaloids (N. Y.) 1986, 28, 183-308. Michael, J. P. Natural Products Reports 1990, 485-513. Rajeswari, S.; Chandrasekharan, S.; Govindachari, R.; Heterocycles, 1987, 25, 659-700.
14. 9. For recent reviews on the chemistry and biology of polyhidroxyindolizidine alkaloids, see: Elbein, A. D.; Molyneux, R. J., Alkaloids: Chemical and Biological perspectives; Pelletier, S. W.; Ed.; Wiley; New York, 1987; vol. 5, chapter 1, pp. 1-54. Howard, A. S.; Michael, J. P. Alkaloids (N. Y.) 1986, 28, 183-308. Michael, J. P. Natural Products Reports 1990, 485-513. Rajeswari, S.; Chandrasekharan, S.; Govindachari, R.; Heterocycles, 1987, 25, 659-700.
15. 9. For recent reviews on the chemistry and biology of polyhidroxyindolizidine alkaloids, see: Elbein, A. D.; Molyneux, R. J., Alkaloids: Chemical and Biological perspectives; Pelletier, S. W.; Ed.; Wiley; New York, 1987; vol. 5, chapter 1, pp. 1-54. Howard, A. S.; Michael, J. P. Alkaloids (N. Y.) 1986, 28, 183-308. Michael, J. P. Natural Products Reports 1990, 485-513. Rajeswari, S.; Chandrasekharan, S.; Govindachari, R.; Heterocycles, 1987, 25, 659-700.
16. 9. For recent reviews on the chemistry and biology of polyhidroxyindolizidine alkaloids, see: Elbein, A. D.; Molyneux, R. J., Alkaloids: Chemical and Biological perspectives; Pelletier, S. W.; Ed.; Wiley; New York, 1987; vol. 5, chapter 1, pp. 1-54. Howard, A. S.; Michael, J. P. Alkaloids (N. Y.) 1986, 28, 183-308. Michael, J. P. Natural Products Reports 1990, 485-513. Rajeswari, S.; Chandrasekharan, S.; Govindachari, R.; Heterocycles, 1987, 25, 659-700.
17. 10. VanRhenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett., 1976, 1973-1976.
18. 11. For a similar case, see: Oishi T.; Iwakuma T.; Hirama M.; Ito S., Synlett, 1995, 404-406.
19. 1H NMR spectrum of 14 when the equatorial H-8 (δ: 2.34 ppm) was irradiated. (equation presented)
20. 3): 19.52 (t); 20.96 (t); 24.82 (q); 26.07 (q); 38.42 (t); 72.96 (d); 75.69 (d); 103.38 (d); 112.22 (s); 135.42(s); 168.78 (s) ppm.
21. 9 in quantitative yield.
22. 9