An expedient synthesis of 7(S)-ethyl-8(R or S)-indolizidinols based on a thiophene reductive desulfurization

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 697-702

  Marchalín, Štefan ^a   Žúžiová, Jozefína ^a   Kadlečíková, Katarína ^a   Šafář, Peter ^a   Baran, Peter ^b   Dalla, Vincent ^c   Daïch, Adam ^c  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b JUNIATA COLLEGE   (United States)

^c UNIVERSITÉ DU HAVRE   (France)

Author keywords

Alkaloid; Bioactive product; Chiron approach; Desulfurization; Diastereoselective; Heterocycle; Indolizidinol; Raney nickel; Reduction

Indexed keywords

4 HYDROXYTHIENOINDOLIZIN 7 ONE; 7 ETHYL 8 INDOLIZIDINOL DERIVATIVE; CASTANOSPERMINE; ELAEOKANINE; HEXAHYDROTHIENO[2,3 F]INDOLIZINE 4,7 DIONE; INDOLIZIDINE ALKALOID; INDOLIZIDINOL; LENTIGINOSINE; NEUROTOXIN; PUMILIOTOXIN; SWAINSONINE; THIENOINDOLIZINE 4,7 DIONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DESULFURIZATION; ENZYME INHIBITION; ISOMER; MITSUNOBU REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CHIRON;

EID: 33845793338     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.092     Document Type: Article

References (72)

1. For leading reviews in this field, see:. Pyne S.G. Curr. Org. Synth. 2 (2005) 39-57
2. El Nemr A.E. Tetrahedron 56 (2000) 8579-8629
3. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
4. Elbein A.D., and Molyneux R.J. Alkaloid Glycosidase Inhibitors. In: Barton D., Nakanishi K., and Meth-Cohn O. (Eds). Comprehensive Natural Products Chemistry Vol. 3 (1999), Elsevier, Oxford 129
5. Sears P., and Wong C.-H. Chem. Commun. (1998) 1161-1170
6. Ganem B. Acc. Chem. Res. 29 (1996) 340-347
7. Dwek R.A. Chem. Rev. 96 (1996) 683-720
8. Kaushal G.P., and Elbein A.D. Methods Enzymol. 230 (1994) 316-329
9. Look G.C., Fotsch C.H., and Wong C.-H. Acc. Chem. Res. 26 (1993) 182-190
10. Legler G. Adv. Carbohydr. Chem. Biochem. 48 (1990) 319-384
11. Sinnot M.L. Chem. Rev. 90 (1990) 1171-1202
12. See, for example:. In: Barton D.H.B., and Nakanishi K. (Eds). Comprehensive Natural Products Chemistry. Vol. 4 (1999), Elsevier Science, Oxford 25
13. Dewick P.M. Medicinal Natural Products. (1998), Wiley p 289
14. Mikael J.P. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 16 (1999) 675-709
15. For recent syntheses of castanospermine, see:. Karanjule N.S., Markad S.D., Shinde V.S., and Dhavale D.D. J. Org. Chem. 71 (2006) 4667-4670
16. Cronin L., and Murphy P.V. Org. Lett. 7 (2005) 2691-2693
17. For recent syntheses of swainsonine, see:. Martin R., Murruzzu C., Pericas M.A., and Riera A. J. Org. Chem. 70 (2005) 2325-2328
18. Carmona A.T., Fuentes J., Robina I., Garcia E.R., Demange R., Vogel P., and Winters A.L. J. Org. Chem. 68 (2003) 3874-3883
19. For recent syntheses of lentigenisine, see:. Kim I.S., Zee O.P., and Jung J.H. Org. Lett. 8 (2006) 4401-4404
20. Chaudhari V.D., Ajish Kumar K.S., and Dhavale D.D. Tetrahedron 62 (2006) 4354-4359
21. For reviews and articles related to this subject, see:. Daly J.W., Brown G.B., Mensah-Dwumah M., and Myers C.W. Toxicon 16 (1978) 163-188
22. Witkop B., and Gössinger E. In: Bossi A. (Ed). The Alkaloids: Chemistry and Pharmacology Vol. 21 (1983), Academic Press, New York 139-253
23. Daly J.W., Garraffo H.M., and Spande T.F. Alkaloids Vol. 43 (1993), Academic Press, New York 185
24. Daly J.W. J. Med. Chem. 46 (2003) 445-452
25. Daly J.W., Spande T.F., and Garraffo H.M. J. Nat. Prod. 68 (2005) 1556-1575
26. Hart N.K., Johns S.R., and Lamberton J.A. Aust. J. Chem. 25 (1972) 817-835
27. Lee H.K., Chun J.S., and Pak C.S. J. Org. Chem. 68 (2003) 2471-2474
28. Lee Y.S., Kim D.W., Lee J.Y., Jeong K.S., and Pak H. Bull. Korean Chem. Soc. 19 (1998) 8-9
29. Rasmussen M.O., Delair P., and Greene A.E. J. Org. Chem. 66 (2001) 5438-5443
30. Clavestine E.C., Walter P., Harris T.M., and Broquist H.P. Biochemistry 18 (1979) 3663-3667
31. Harris C.M., and Harris T.M. Tetrahedron Lett. 28 (1987) 2559-2592
32. Shono T., Kise N., and Tanabe T. J. Org. Chem. 53 (1988) 1364-1367
33. Harris C.M., Schneider M.J., Ungemach F.S., Hill J.E., and Harris T.M. J. Am. Chem. Soc. 110 (1988) 940-949
34. Takahata H., Banba Y., and Momose T. Tetrahedron: Asymmetry 1 (1990) 763-764
35. Harris T.M., Harris C.M., Hill J.E., Ungemach F.S., Broquist H.P., and Wickwire B.M. J. Org. Chem. 52 (1987) 3094-3098
36. Harris C.M., Campbell B.C., Molyneux R.J., and Harris T.M. Tetrahedron Lett. 29 (1988) 4815-4818
37. Pastuszak I., Molyneux R.J., James L.F., and Elbein A.D. Biochemistry 29 (1990) 1886-1891
38. Pearson W.H., and Guo L. Tetrahedron Lett. 42 (2001) 8267-8271
39. Pearson W.H., and Hembre E.J. Tetrahedron Lett. 42 (2001) 8273-8276
40. For another attractive route to enantiopure carbon and hetero-7-substituted swainsonine analogues, see:. Tinarelli A., and Paolucci C. J. Org. Chem. 71 (2006) 6630-6633
41. Fujita T., Nagasawa H., Uto Y., Hashimoto T., Asakawa Y., and Hori H. Org. Lett. 6 (2004) 827-830
42. Le Bosquain D., and Decroix B. Heterocycles 36 (1993) 2303-2314
43. Marchalín S., Szemes F., Bar N., and Decroix B. Heterocycles 50 (1999) 445-452
44. Marchalín S., Decroix B., and Morel J. Acta Chem. Scand. 47 (1993) 287-291
45. Daïch A., and Decroix B. J. Heterocycl. Chem. 33 (1996) 873-878
46. Pigeon P., and Decroix B. Tetrahedron Lett. 37 (1996) 7707-7710
47. Othman M., Pigeon P., and Decroix B. Tetrahedron 53 (1997) 2495-2504
48. Kadlečíková K., Marchalín S., Baran P., Dalla V., and Decroix B. Tetrahedron 61 (2005) 4743-4754
49. Szemes F., Marchalín S., Bar N., and Decroix B. J. Heterocycl. Chem. 35 (1998) 1371-1375
50. Szemes F., Kadlečíková K., Marchalín S., Bobošíková M., Dalla V., and Daïch A. Tetrahedron: Asymmetry 15 (2004) 1763-1770
51. For X-ray analysis of product 12, see:. Lokaj J., Kettmann V., and Marchalin S. Acta Cryst. C55 (1999) 1103-1105
52. For representative examples using this protocol, see:. Michelliza S., Al-Mourabit A., Gateau-Olesker A., and Marazano C. J. Org. Chem. 67 (2002) 6474-6478
53. Gol'Dfarb Y.L., Fabrichnyi B.P., and Shalavina I.F. Tetrahedron 18 (1961) 21-36
54. Badger G.M., Rodda H.J., and Sasse W.H.F. J. Chem. Soc. (1954) 4162-4167
55. For stereoselective reduction of 2,3-disubstituted and 2,3,4,5-tetrasubstituted thiophenes, see:. Jacobi P.A., and Frechette R.F. Tetrahedron Lett. 28 (1987) 2937-2940
56. Jacobi P.A., Egberston M., Frechette R.F., Miao C.K., and Weiss K.T. Tetrahedron 44 (1988) 3327-3338
57. Crenshaw R.R., Luke G.M., Jenks T.A., Partyka R.A., Bialy G., and Bierwagen M.E. J. Med. Chem. 16 (1973) 813-823
58. Collins M.A., and Neville-Jones D. Tetrahedron Lett. 36 (1995) 4467-4470
59. 2 (183.25) C, 65.54; H, 9.35; N, 7.64. Found C, 65.42; H, 9.15; N, 7.49.
60. Full crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC references numbers 614535 and 614534 for products (7S,8S,8aS)-14 and (7S,8R,8aS)-20), respectively. Copies of the data can be obtained free of charge at http://www.ccdc.cam.ac.uk.
61. 21a hydrogenation over an appropriate catalyst led to the formation of the 8S epimer in good stereoselectivity (manuscript under preparation).
62. 19NO (169.27): C, 70.96; H, 11.31; N, 8.27. Found: C, 70.79; H, 11.23; N, 8.18.
63. For various examples, see:. Becker S., Fort Y., Vanderesse R., and Caubère P. J. Org. Chem. 54 (1989) 4848-4853
64. The stereochemistries of 14 were determined on the basis of both the X-ray analysis of (7S,8S,8aS)-14 and their NMR study obtained separately from ketone 12 and alcohol 13, respectively. The ratio of lactams 16 cis and trans was determined by using NOE measurements.
65. Ranade V.S., Consiglio G., and Prins R. J. Org. Chem. 65 (2000) 1132-1138
66. MaGee D.I., Lee M.L., and Decken A. J. Org. Chem. 64 (1999) 2549-2554
67. Ranade V.S., Consiglio G., and Prins R. J. Org. Chem. 64 (1999) 8862-8867
68. 2 (183.25) C, 65.54; H, 9.35; N, 7.64. Found C, 65.42; H, 9.15; N, 7.49.
69. Mitsunobu O. Synthesis (1981) 1-28
70. Martin S.F., and Dodge J.A. Tetrahedron Lett. 32 (1991) 3017-3020
71. Crimmins M.T., Pace J.M., Nantermet P.G., Kim-Meade A.S., Thomas J.B., Watterson S.H., and Wagman A.S. J. Am. Chem. Soc. 121 (1999) 10249-10250
72. 2 (273.38) C, 74.69; H, 8.48; N, 5.12. Found C, 74.51; H, 8.39; N, 5.01.