Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

Tetrahedron

Volumn 52, Issue 7, 1996, Pages 2603-2628

  Louwrier, Saskia ^a   Ostendorf, Martin ^a   Boom, Arnoud ^a   Hiemstra, Henk ^a   Speckamp, W Nico ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LACTAM DERIVATIVE; PTILOMYCALIN A; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030069493     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01085-8     Document Type: Article

References (54)

1. (a) Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925.
2. (b) Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472.
3. (c) Ohtani, I.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2525.
4. Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De brosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westly, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182.
5. Palagiano, E.; De Marino, S.; Minale, L.; Riccio, R.; Zollo, F.; Iorizzi, M.; Lucarain, L.; Provost, J. Tetrahedron, 1995, 57, 3675.
6. (a) Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712.
7. (b) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007.
8. (c) Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805.
9. (a) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Hallenga, K.; Ottinger, R.; Bruno, I.; Riccio, R. Tetrahedron Lett. 1990, 31, 6531.
10. (b) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Rogeau, D.; Amade, P. J. Nat. Prod. 1993, 56, 528.
11. (c) Jares-Erijman, E. A.; Ingrum, A. A.; Sun, F.; Rinehart, K. L. J. Nat. Prod. 1993, 56, 2186.
12. Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657.
13. (a) Snider, B. B.; Shi, Z. Tetrahedron Lett. 1993, 34, 2099.
14. (b) Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1994,116, 549.
15. (c) Murphy, P. J.; Williams, H. L.; Hursthouse, M. B.; Malik, K. M. A. J. Chem. Soc. Chem. Commun. 1994, 119.
16. (d) Murphy, P. J.; Williams, H. L. J. Chem. Soc. Chem. Commun. 1994, 819.
17. (e) Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1993, 58, 3235.
18. (f) Grillot, A. L.; Hart, D. J. Tetrahedron 1995, 51, 11377.
19. (a) Hiemstra, H.; Speckamp, W. N. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds;Pergamon Press: Oxford, 1991; vol. 2, pp. 1047-1082 and references cited therein,
20. (b) Hiemstra, H.; Speckamp, W. N.; in The Alkaloids; Brossi, A.; Ed.; Academic Press: New York, 1988, Vol. 32, p 271.
21. (c) De Koning, H.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. in Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Bioactive Natural Products (Part A); Elsevier: Amsterdam, 1993, Vol. 13, pp 473.
22. (c) De Koning, H.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. in Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Bioactive Natural Products (Part A); Elsevier: Amsterdam, 1993, Vol. 13, pp 473.
23. Koot, W. J.; Van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401.
24. For the first report see: Louwrier, S.; Ostendorf, M.; Hiemstra, H.; Speckamp, W. N. Book of Abstracts, 33rd National Organic Chemistry Symposium of the American Chemical Society, Bozeman, Montana; 1993; p 326.
25. Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653.
26. (a) Thaning, M.; Wistrand, L. G. J. Org. Chem. 1990, 55, 1406.
27. (b) Thaning, M.; Wistrand, L. G. Acta Chem. Scand. 1989, 43, 290.
28. Krägeloh, K.; Simchen, G. Synthesis 1981, 30.
29. Gilbert, J. C.; Kelly, T. A. Tetrahedron 1988, 44, 7587.
30. Bernardi, A.; Michelli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949.
31. (a) Keum, G.; Kim, G. Bull. Korean Chem. Soc. 1994, 75, 278.
32. (b) Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
33. Huszthy, P.; Oue, M.; Bradshaw, J. S.; Zhu, C. Y.; Wang, T.; Dalley, N. K.; Curtis, J. C.; Izatt, R. M. J. Org. Chem. 1992, 57, 5383.
34. (a) Maemoto, S.; Mori, K. Chem. Lett. 1987, 109.
35. (b) Gerlach, H. G.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755.
36. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd Ed, Wiley: New York, 1991, (pp 83-84 and 414-416).
37. (a) Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 99.
38. (b) Brooks, D. W.; Kellogg, R. P.; Cooper, C. S. J. Org. Chem. 1987, 52, 192.
39. (c) Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975.
40. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
41. Krapcho, A.P. Synthesis 1982, 805.
42. Lloris, M. E.; Moreno-Mañas, M. Tetrahedron Lett. 1993, 34, 7119.
43. (a) Yoshimura, J.; Yamaura, M.; Suzuki, T.; Hasimoto, H. Chemistry Lett. 1983, 1001.
44. (b) Yamaura, M.; Suzuki, T.; Hasimoto, H.; Yoshimura, H.; Okamoto, T.; Shin, C. Bull. Chem. Soc. Jpn. 1985, 58, 1413.
45. (c) Williams, R. M.; Armstrong, R. W.; Maruyama, L. K.; Dung, J. S.; Anderson, O. P. J. Am. Chem. Soc. 1985, 107, 3246.
46. Smith III, A. B.; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc 1992, 114, 2995.
47. (a) Barton, D. H. R.; Motherwell, W. B. Pure Appl. Chem. 1981, 53, 15.
48. (b) Hartwig, W. Tetrahedron 1983, 39, 2609.
49. (c) Robins, M. J.; Wilson, J. S.; Hanske, F. J. Am. Chem. Soc. 1983, 105, 4059.
50. In the case of an unprotected β-ketoester, an undesired side reaction between the β-ketoester and the C-3 substituent could not be prevented.
51. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
52. Shono, T.; Matsumura, Y.; Uchida, K.; Tsuata, K.; Makino, A. J. Org. Chem. 1984, 49, 300.
53. Najera, C.; Yus, M.; Seebach, D. Helv. Chim. Acta 1984, 67, 289
54. Gerlach, H. G.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755.