Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3α-benzene-sulfenate

Synlett

Volumn , Issue 5, 1999, Pages 635-637

  Petrović, Goran ^a   Saičić, Radomir N ^a   Čeković, Živorad ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

1,5 hydrogen shift; 6,7 Dehydrotropine; Intramolecular radical reaction; Scopine; Tropine benzenesulfenate

Indexed keywords

6,7 DEHYDROTROPINE; ACETYL SCOPINE; SCOPOLAMINE DERIVATIVE; TROPINE; TROPINE BENZENESULFENATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; ESTERIFICATION; OXIDATION; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141894152     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2658     Document Type: Article

References (38)

1. Fodor, G. Prog. Phytochem., 1968, 1, 491; Experientia, 1955, 11, 129; Tetrahedron, 1957, 1, 86; Chem. Ind. (London), 1961, 1500; Tropane Alkaloids in Chemistry of the Alkaloids, Pelletier, S. W., Ed. Van Nostrand-Reinhold, Princeton, N. J. 1970, Chapter 15.
2. Fodor, G. Prog. Phytochem., 1968, 1, 491; Experientia, 1955, 11, 129; Tetrahedron, 1957, 1, 86; Chem. Ind. (London), 1961, 1500; Tropane Alkaloids in Chemistry of the Alkaloids, Pelletier, S. W., Ed. Van Nostrand-Reinhold, Princeton, N. J. 1970, Chapter 15.
3. Fodor, G. Prog. Phytochem., 1968, 1, 491; Experientia, 1955, 11, 129; Tetrahedron, 1957, 1, 86; Chem. Ind. (London), 1961, 1500; Tropane Alkaloids in Chemistry of the Alkaloids, Pelletier, S. W., Ed. Van Nostrand-Reinhold, Princeton, N. J. 1970, Chapter 15.
4. Fodor, G. Prog. Phytochem., 1968, 1, 491; Experientia, 1955, 11, 129; Tetrahedron, 1957, 1, 86; Chem. Ind. (London), 1961, 1500; Tropane Alkaloids in Chemistry of the Alkaloids, Pelletier, S. W., Ed. Van Nostrand-Reinhold, Princeton, N. J. 1970, Chapter 15.
5. Fodor, G. Prog. Phytochem., 1968, 1, 491; Experientia, 1955, 11, 129; Tetrahedron, 1957, 1, 86; Chem. Ind. (London), 1961, 1500; Tropane Alkaloids in Chemistry of the Alkaloids, Pelletier, S. W., Ed. Van Nostrand-Reinhold, Princeton, N. J. 1970, Chapter 15.
6. a) Fodor, G.; Toth, J.; Koczor, I.; Dobo, P.; Vincze, I. Chem. Ind. (London), 1956, 764;
7. b) Fodor, G.; Toth, J.; Koczor, I. Chem. Ind. (London), 1955, 1260;
8. c) Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. J. Am. Chem. Soc., 1978, 100, 1786.
9. a) Dobo, P.; Fodor, G.; Janzso, G.; Koczor, I.; Toth, J.; Vincze, I. J. Chem. Soc., 1959, 3461;
10. b) Fodor, G.; Toth, J.; Romeike, A.; Vincze, I.; Dobo, P.; Janzso, G. Angew. Chem., 1957, 69, 678.
11. a) Stoll, A.; Lindenmann, A.; Jucker, E. Helv. Chim. Acta, 1953, 36, 1506, 1526;
12. b) Meinwald, J.; Chapman, O. L. J. Am. Chem. Soc., 1957, 79, 665;
13. c) Willstatter, R.; Berner, E. Chem. Ber., 1923, 56, 1079;
14. d) Cowling, A. P.; Mann, J. J. Chem. Soc. Perkin Trans. 1, 1978, 1564.
15. Petrović, G.; Saičić, R. N.; Čeković, Ž. Tetrahedron Lett., 1997, 38, 7107.
16. a) Petrović, G.; Čeković, Ž. Tetrahedron Lett., 1997, 38, 627;
17. b)Mihailović, M. Lj.; Čeković, Ž. Synthesis, 1970, 209;
18. c) Majetich, G.; Wheless, K. J. Tetrahedron (Report No 375), 1995, 51, 7095;
19. d) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc., 1961, 83, 4076;
20. e) Barton, D. H. R. Pure and Appl. Chem., 1968, 16, 1; Hesse, R. H. Advan. in Free Radical Chem. 1969, 3, 83.
21. e) Barton, D. H. R. Pure and Appl. Chem., 1968, 16, 1; Hesse, R. H. Advan. in Free Radical Chem. 1969, 3, 83.
22. Khuong-Huu, F.; Bennett, C. R.; Fouche, D. E.; Goutarel, G. C. R. Acad. Sci. Paris Serie C, 1972, 275, 499.
23. Intramolecular functionalization of tropine by hypoiodite and hypobromite reactions, as well as by lead tetraacetate and phenyliodoso diacetate oxidation have not been achieved; Čeković, Ž. et al. unpublished results.
24. Maryanoff, B. E.; Almond, Jr., H. R. J. Org. Chem., 1986, 51, 3295; Kraiss, G.; Nador, K. Tetrahedron Lett., 1971, 57.
25. Maryanoff, B. E.; Almond, Jr., H. R. J. Org. Chem., 1986, 51, 3295; Kraiss, G.; Nador, K. Tetrahedron Lett., 1971, 57.
26. 3S: C, 62.54; H, 6.84; N, 4.56; Found: C, 62.68; H, 7.05; N, 4.42.
27. 3S: C, 62.54; H, 6.84; N, 4.56; Found: C, 62.68; H, 7.05; N, 4.42.
28. 3S: C, 62.54; H, 6.84; N, 4.56; Found: C, 62.68; H, 7.05; N, 4.42.
29. 3S: C, 62.54; H, 6.84; N, 4.56; Found: C, 62.68; H, 7.05; N, 4.42.
30. 3S: C, 62.54; H, 6.84; N, 4.56; Found: C, 62.51; H, 6.71; N, 4.44. In addition to compound 6, 0.15 g (15%) of N-carbethoxy nortropinone 7 and 0.36 g (37%) of alcohol 4 were also isolated.
31. Trost, B. M.; Salzmann, T. N. J.; Hiroi, K. J. Am. Chem. Soc., 1976, 98, 4887.
32. a) Trost, B. M.; Salzmann, T. N. J.; J. Org. Chem., 1975, 40. 148; Grieco P. A.; Miyashita, M. J. Org. Chem., 1974, 39, 120; Sharpless, K. B.; Young, M. W. J. Org, Chem., 1975, 40, 947.
33. a) Trost, B. M.; Salzmann, T. N. J.; J. Org. Chem., 1975, 40. 148; Grieco P. A.; Miyashita, M. J. Org. Chem., 1974, 39, 120; Sharpless, K. B.; Young, M. W. J. Org, Chem., 1975, 40, 947.
34. a) Trost, B. M.; Salzmann, T. N. J.; J. Org. Chem., 1975, 40. 148; Grieco P. A.; Miyashita, M. J. Org. Chem., 1974, 39, 120; Sharpless, K. B.; Young, M. W. J. Org, Chem., 1975, 40, 947.
35. 3: C, 60.89; H, 7.66; N, 7.10; Found: C, 60.52; H, 7.40; N, 7.54.
36. +-AcO) 98%.
37. a) Petrović, G.; Čeković, Ž. Tetrahedron, 1999, 55, 1377.
38. ++1) 100%.