Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

Tetrahedron Asymmetry

Volumn 14, Issue 19, 2003, Pages 3019-3031

  Hartung, Jens ^a,b   Kneuer, Rainer ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 BENZOYLOXY 5 BROMOMETHYL 2 METHYLTETRAHYDROFURAN; ALKALOID DERIVATIVE; ALLOMUSCARINE; BROMINE DERIVATIVE; EPIALLOMUSCARINE; EPIMUSCARINE; KETONE DERIVATIVE; MUSCARINE; MUSCARINIC AGENT; N (3 BENZOYLOXY 5 HEXEN 2 OXY) 4 METHYLTHIAZOLE 2(3H) THIONE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; TEMPERATURE DEPENDENCE;

EID: 1542382741     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.06.006     Document Type: Article

References (71)

1. Waser P.G. Pharmacol. Rev. 13:1961;465-515.
2. Eugster C.H., Waser P.G. Experientia. 10:1954;298-300.
3. Wilkinson S. Quart. Rev. Chem. Soc. 15:1961;153-171.
4. Eugster C.H. Naturwissenschaften. 55:1968;305-313.
5. Bollinger H., Eugster C.H. Helv. Chim. Acta. 54:1971;2704-2730.
6. Eugster C.H. Helv. Chim. Acta. 39:1956;1002-1023.
7. Kögl F., Salemink C.A., Schouten H., Jellinek F. Recl. Trav. Chim. Pays Bas. 76:1957;109-127.
8. Nitta K., Stadelmann R.J., Eugster C.H. Helv. Chim. Acta. 60:1977;1747-1753.
9. Bollinger H., Eugster C.H. Helv. Chim. Acta. 54:1971;1332-1335.
10. Catalformo P., Eugster C.H. Helv. Chim. Acta. 53:1970;848-851.
11. List H.P., Müller H. Arch. Pharm. 292:1959;777-787.
12. Eugster C.H., Müller G. Helv. Chim. Acta. 42:1959;1189-1190.
13. Kang K.H., Cha M.Y., Pae N.A., Choi K.I., Cho Y.S., Koh H.Y., Chung B.Y. Tetrahedron Lett. 41:2000;8137-8140.
14. Takano S., Iwabuchi Y., Ogasawara K. J. Chem. Soc. Chem. Commun. 1989;1371-1372.
15. Mulzer J., Angermann A., Münch W., Schlichthörl G., Hentzschel A. Liebigs Ann. Chem. 1987;7-14.
16. Amouroux R., Gerin B., Chastrette M. Tetrahedron. 41:1985;5321-5324.
17. Still W.C., Schneider J.A. J. Org. Chem. 45:1980;3375-3376.
18. Wang P.-C., Joullié M.M. Brossi A. The Alkaloids. 23:1984;327-380 Academic Press, New York.
19. Lewis J.R. Nat. Prod. Rep. 15:1998;417-437.
20. Lewis J.R. Nat. Prod. Rep. 15:1998;371-395.
21. Norrild J.C., Pedersen C. Synthesis. 1997;1128-1130.
22. Popsavin V., Beric O., Csanádi J., Popsavin M., Miljkovic D. J. Serb. Chem. Soc. 60:1995;625-628.
23. Chmielewski M., Guzik P., Hintze B., Daniewski W.M. J. Org. Chem. 50:1985;5360-5362.
24. Fronza G., Fuganti C., Grasselli P. Tetrahedron Lett. 19:1978;3941-3942.
25. Corrodi H., Hardegger E., Kögl F. Helv. Chim. Acta. 40:1957;2454-2461.
26. Angle S.R., El-Said N.A. J. Am. Chem. Soc. 124:2002;3608-3613.
27. Popsavin V., Beric O., Popsavin M., Radic L., Csanádi J., Cirin-Novta V. Tetrahedron. 56:2000;5929-5940.
28. Popsavin V., Beric O., Popsavin M., Lajsic S., Miljkovic D. Carbohaydr. Lett. 3:1998;1-8.
29. Popsavin V., Beric O., Popsavin M., Csanádi J., Miljkovic D. Carbohydr. Res. 269:1995;343-347.
30. Oshiba Y., Yoshimitsu T., Ogasawara K. Chem. Pharm. Bull. 43:1995;1067-1069.
31. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
32. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
33. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
34. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
35. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
36. From L-arabinose: (a) Hardegger. E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383-2389; From L-rhamnose: (b) Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023-3027; From 2-deoxy-L-ribose: (c) Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193-198; From D-mannose: (d) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809-813; (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401-2410; From D-glucosamine: (f) Cox H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229-235.
37. For example, see: (a) Knight, D. W.; Shaw. D.; Fenton, G. Synlett 1994, 295-296; (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726-2729; (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341-4344.
38. For example, see: (a) Knight, D. W.; Shaw. D.; Fenton, G. Synlett 1994, 295-296; (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726-2729; (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341-4344.
39. For example, see: (a) Knight, D. W.; Shaw. D.; Fenton, G. Synlett 1994, 295-296; (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726-2729; (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341-4344.
40. Hartung J., Kunz P., Laug S., Schmidt P. Synlett. 2003;51-54.
41. Hartung J., Kneuer R. Eur. J. Org. Chem. 2000;1677-1683.
42. Hartung, J.; Kneuer, R.; Laug, S.; Schmidt, P.; Špehar, K.; Svoboda, I.; Fuess, H.; Eur. J. Org. Chem. 2003, in press.
43. Hartung J. Eur. J. Org. Chem. 2001;619-632.
44. Mash E.A., Arterburn J.B., Fryling J.A., Mitchel S.H. J. Org. Chem. 56:1991;1088-1093.
45. Hartung J., Hünig S., Kneuer R., Schwarz M., Wenner H. Synthesis. 1997;1433-1438.
46. Miyashita M., Yoshikoshi A., Grieco P.A. J. Org. Chem. 42:1977;3772-3774.
47. Hartung J., Kneuer R., Schwarz M., Svoboda I., Fuess H. Eur. J. Org. Chem. 1999;97-106.
48. De Amici M., De Micheli C., Molteni G., Pitrè D., Carrea G., Riva S., Spezia S., Zetta L. J. Org Chem. 56:1999;67-72.
49. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543-2549.
50. Hartung J., Kneuer R., Kopf T.M., Schmidt P. CR Acad. Sci. Paris Chim. 2001;649-666.
51. Nozaki K., Oshima K., Utimoto K. J. Am. Chem. Soc. 109:1987;2547-2549.
52. Hartung J., Gottwald T., Špehar K. Synthesis. 2002;1469-1498.
53. Horita K., Yoshioka T., Tanaka T., Oikawa Y., Yonemitsu O. Tetrahedron. 42:1986;3021-3028.
54. Heathcock C.H., Kiyooka S.-I., Blumenkopf T.A. J. Org. Chem. 49:1984;4214-4223.
55. Hartung J., Schwarz M., Svoboda I., Fuess H. Eur. J. Org. Chem. 1999;1275-1290.
56. Walter W., Schaumann E. Synthesis. 1971;111-130.
57. Chimiak A., Przychodzen W., Rachon J. Heteratom. Chem. 13:2002;169-194.
58. Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds. 1986;2-35 Pergamon Press, Oxford.
59. Hartung J., Gallou F. J. Org. Chem. 60:1995;6706-6716.
60. Adam W., Hartung J., Okamoto H., Marquardt S., Nau W.M., Pischel U., Saha-Möller C.R., Špehar K. J. Org. Chem. 67:2002;6041-6049.
61. 14→15b. For fundamentals of this correlation see: Giese B., Keller K. Chem. Ber. 112:1979;1743-1750. and references cited therein.
62. Hartung, J.; Stowasser, R.; Vitt, D.; Bringmann, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2820-2823; Angew. Chem. 1996, 108, 3056-3059
63. Hartung, J.; Stowasser, R.; Vitt, D.; Bringmann, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2820-2823; Angew. Chem. 1996, 108, 3056-3059
64. Beckwith A.L.J., Schiesser C. Tetrahedron. 41:1985;3925-3941.
65. Spellmeyer D.C., Houk K.N. J. Org. Chem. 52:1987;959-974.
66. The terms axial and equatorial have originally been coined in order to denote the positions of the substituents in the undistorted chair conformer of cyclohexane. In extension to this definition, axial and equatorial positions have been specified in cyclopentane and its saturated heterocyclic derivatives. These positions are found in twist conformers and refer to exocyclic locations at the two carbon which are transposed above and below the plane that is defined by the remaining three atoms. See: Testa B. Grundlagen der Organischen Chemie. 1983;103-104 VCH, Weinheim.
67. Corminboeuf O., Renaud P., Schiesser C.H. Chem. Eur. J. 9:2003;1478-1584.
68. For the definition of bisectional positions at cyclopentane and its heterocyclic derivatives, see: Bogner J., Duplan J.-C., Infarnet Y., Delmut J., Huet J. Bull. Chim Soc. Fr. 1972;3616-3624.
69. Kirby A.J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. 1983;Springer, Berlin.
70. Perrin D.D., Armatego W.L.F., Perrin D.R. Purification of Laboratory Chemicals. 2nd ed. 1980;Pergamon Press, Oxford.
71. Barton D.H.R., Crich D., Kretzschmar G. J. Chem. Soc., Perkin Trans. 1. 1986;39-53.