A short enantioselective synthesis of naturally occurring muscarine alkaloids from 1,4-hexadiene

Synlett

Volumn , Issue 1, 2003, Pages 51-54

  Hartung, Jens ^a   Kunz, Patricia ^a   Laug, Stefanie ^a   Schmidt, Philipp ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Bromide; Cyclization; Muscarine alkaloids; Oxidation; Tetrahydrofuran; Vanadium

Indexed keywords

1,4 HEXADIENE; ALKADIENE; ALKALOID; MUSCARINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIHYDROXYLATION; ENANTIOSELECTIVITY; OXIDATION; SYNTHESIS;

EID: 0037242514     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (58)

1. (a) Wang, P.-C.; Joullié, M. M. In The Alkaloids, Vol. 23; Brossi, A., Ed.; Academic Press: New York, 1984, 327-380.
2. (b) Lewis, J. R. Nat. Prod. Rep. 1998, 15, 417.
3. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 15, 371.
4. (a) Eugster, C. H.; Waser, P. G. Experientia 1954, 10, 298.
5. (b) Eugster, C. H. Naturwissenschaften 1968, 55, 305.
6. (a) Bollinger, H.; Eugster, C. H. Helv. Chim. Acta 1971, 54, 2704.
7. (b) Eugster, C. H. Helv. Chim. Acta 1956, 39, 1002.
8. Kögl, F.; Salemink, C. A.; Schouten, H.; Jellinek, F. Recl. Trav. Chim. Pays Bas 1957, 76, 109.
9. Nitta, K.; Stadelmann, R. J.; Eugster, C. H. Helv. Chim. Acta 1977, 60, 1747.
10. (a) Bollinger, H.; Eugster, C. H. Helv. Chim. Acta 1971, 54, 1332.
11. (b) Catalformo, P.; Eugster, C. H. Helv. Chim. Acta 1970, 53, 848.
12. (c) List, H. P.; Müller, H. Arch. Pharm. (Weinheim, Ger.) 1959, 292, 777.
13. (d) Eugster, C. H.; Müller, G. Helv. Chim. Acta 1959, 42, 1189.
14. Waser, P. G. Pharmacol. Res. 1961, 13, 465.
15. Wilkinson, S. Quart. Rev. Chem. Soc. 1961, 15, 153.
16. Eugster, C. H.; Schleusener, E. Helv. Chim. Acta 1969, 52, 708.
17. (a) Kang, K. H.; Cha, M. Y.; Pae, N. A.; Choi, K. I.; Cho, Y. S.; Koh, H. Y.; Chung, B. Y. Tetrahedron Lett. 2000, 41, 8137.
18. (b) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1371.
19. (c) Mulzer, J.; Angermann, A.; Münch, W.; Schlichthörl, G.; Hentzschel, A. Liebigs Ann. Chem. 1987, 7.
20. (d) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron 1985, 41, 5321.
21. (e) Still, W. C.; Schneider, J. A. J. Org. Chem. 1980, 45, 3375.
22. (f) Hardegger, E.; Lohse, F. Helv. Chim. Acta 1957, 40, 244.
23. (a) Norrild, J. C.; Pedersen, C. Synthesis 1997, 1128.
24. (b) Popsavin, V.; Beric, O.; Csanádi, J.; Popsavin, M.; Miljkovic, D. J. Serb. Chem. Soc. 1995, 60, 625.
25. (c) Chmielewski, M.; Guzik, P.; Hintze, B.; Daniewski, W. M. J. Org. Chem. 1985, 50, 5360.
26. (d) Fronza, G.; Fuganti, C.; Grasselli, P. Tetrahedron Lett. 1978, 3941.
27. (e) Corrodi, H.; Hardegger, E.; Kögl, F. Helv. Chim. Acta 1957, 40, 2454.
28. (a)Angle, S. R.; El-Said, N. A. J. Am. Chem. Soc. 2002, 124, 3608.
29. (b) Popsavin, V.; Beric, O.; Popsavin, M.; Radic, L.; Csanádi, J.; Cirin-Novta, V. Tetrahedron 2000, 56, 5929.
30. (c) Popsavin, V.; Beric, O.; Popsavin, M.; Lajsic, S.; Miljkovic, D. Carbohydr. Lett. 1998, 3, 1.
31. Popsavin, V.; Beric, O.; Popsavin, M.; Csanádi, J.; Miljkovic, D. Carbohydr. Res. 1995, 269, 343.
32. De Amici, M.; Dallanoce, C.; De Micheli, C.; Grana, E.; Barbieri, A.; Ladinsky, H.; Schiavi, G.; Zonta, F. J. Med. Chem. 1992, 35, 1915; and references cited therein.
33. (a) From L-arabinose: Hardegger, E.; Lohse, F. Helv. Chim. Acta 1957, 40, 2383.
34. (b) From L-rhamnose: Mantell, S. J.; Fleet, G. W. J.; Brown, D. J. Chem. Soc., Perkin Trans. 1 1992, 3023.
35. (c) From 2-deoxy-L-ribose: Pochet, S.; Huynh-Dinh, T. J. Org. Chem. 1982, 47, 193.
36. (d) From D-mannose: Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809.
37. (e) Hardegger, E.; Furter, H.; Kiss, J. Helv. Chim. Acta 1958, 41, 2401.
38. (f) From D-glucosamine: Cox, H. C.; Hardegger, E.; Kögl, F.; Liechti, P.; Lohse, F.; Salemink, C. A. Helv. Chim. Acta 1958, 41, 229.
39. For examples: (a) Knight, D. W.; Shaw, D.; Fenton, G. Synlett 1994, 295. (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726. (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341.
40. For examples: (a) Knight, D. W.; Shaw, D.; Fenton, G. Synlett 1994, 295. (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726. (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341.
41. For examples: (a) Knight, D. W.; Shaw, D.; Fenton, G. Synlett 1994, 295. (b) Chan, T. H.; Li, C. J. Can. J. Chem. 1992, 70, 2726. (c) Amouroux, R.; Gerin, B.; Chastrette, M. Tetrahedron Lett. 1982, 23, 4341.
42. (Z)-1,4-Hexadiene(2) (Fluka) (E)-1,4-hexadiene(4) (Chemsampco) are commercially available and were used as recieved.
43. 6], 1,4-bis(9-O-dihydroquinidyl)phthalazine. For a review on the AD reaction, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
44. (b) For enantioselective dihydroxylations of polyenes see: Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345.
45. Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
46. 19 0.69 for -4-hexene-1,2-diol and for (E)-4-hexene-1,2-diol. Ee values of diols 3 and 5 were determined by GC on a β-Dex-325 column (Supelco).
47. Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
48. Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
49. Hale, K. J.; Lennon, J. A.; Manaviazar, S.; Javaid, M. H.; Hobbs, C. J. Tetrahedron Lett. 1995, 36, 1359.
50. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Whang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
51. Hartung, J.; Greb, M.; Špehar, K.; Köhler, F.; Kluge, M.; Csuk, R. in preparation.
52. Mimoun, H.; Mignard, M.; Brechot, P.; Saussine, L. J. Am. Chem. Soc. 1986, 108, 3711.
53. Hartung, J.; Schmidt, P. Synlett 2000, 367.
54. 29 Samples which contained the enantiomers of 6a-d in excess were available from a previous study: Hartung, J.; Kneuer, R. Eur J. Org. Chem. 2000, 1677.
55. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
56. Kirby, A. J. In The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983.
57. 32
58. 25 for the enantioenriched sample which was prepared in the present study using the AD bromocycloetherification sequence is unclear.