Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones. First total synthesis of both enantiomers of pipermethystine

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3381-3383

  Gómez Arrayás, Ramón ^a   Alcudia, Ana ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; KAVA; PIPERMETHYSTINE; PYRIDONE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CHEMISTRY, PHARMACEUTICAL; CYCLIZATION; KAVA; PLANTS, MEDICINAL; PYRIDONES; STEREOISOMERISM;

EID: 0035909647     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010183+     Document Type: Article

References (47)

1. (a) Jones, T. H.; Blum, M. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1983; Vol 1, pp 33-84.
2. (b) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol 3, pp 1-90.
3. (c) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press; Orlando, 1985; Vol. 26, p 89.
4. (d) Daly, J. W. J. Nat. Prod. 1998, 61, 162.
5. (e) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581.
6. (f) Balasubramanian, M.; Deay, J. G. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: New York, 1996; Vol. 5, p 245.
7. (g) Rubiralta, M.; Giralt, E.; Diez, A. In Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives; Elsevier: Amsterdam, 1991.
8. Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
9. Fujita, R.; Watanabe, K.; Ikeura, W.; Ohtake, Y. Hongo,; H. Heterocycles 2000, 53, 2607.
10. Casamitjana, N.; López, V.; Jorge, A.; Bosch, J.; Molins, E.; Roig, A. Tetrahedron 2000, 56, 4027.
11. (a) Grundon, M. F. Nat. Prod. Rep. 1989, 6, 523.
12. (b) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1981; Vol 5, pp 1-54.
13. For the synthesis of 3,4,5-trihydroxylated 2-piperidones, see: (a) Piró, J.; Rubiralta, M.; Giralt, E.; Diez, A. Tetrahedron Lett. 1999, 40, 4865.
14. (b) Defoin, A.; Sarazin, H.; Sifferlen, T.; Strehler, C.; Streith, J. Helv. Chim. Acta 1998, 81, 1417.
15. (c) Bouchez, V.; Stasik, I.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1997, 38, 7733.
16. (d) Norris, P.; Horton, D.; Levine, B. R. Tetrahedron Lett. 1995, 43, 7811.
17. For the synthesis and inhibitory activity of 3,4,5-trihydroxypiperidines, see: (e) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007.
18. (a) Lee, H. K.; Chun, J. S.; Pak, C. S. Tetrahedron Lett. 2001, 42, 3483.
19. (b) Modyanova, L.; Azerad, R. Tetrahedron Lett. 2000, 41, 3865.
20. (c) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 8931.
21. (d) Altenbach, H.-J.; Himmeldirk, K. Tetrahedron: Asymmetry 1995, 6, 1077.
22. Herdeis, C. Synthesis 1986, 232.
23. Herdeis, C.; Kaschinski, C.; Karla, R. Tetrahedron: Asymmetry 1996, 7, 867.
24. (a) Smith, R. Tetrahedron 1979, 35, 437.
25. See also: (b) Smith, R. Phytochemistry 1983, 22, 1055.
26. (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc., in press.
27. (b) Moretto, A. F.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 7445-7455.
28. (c) Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 3909-3911.
29. (d) Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 4083-4086.
30. A previously described procedure for the preparation of β,γ-unsaturated amides was used: Marson, C. M.; Grabowska, U.; Fallah, A.; Walsgrove, T.; Eggleston, D. S.; Baures, P. W. J. Org. Chem. 1994, 59, 291.
31. For a recent review on ring closing metathesis, see (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
32. For previous synthesis of 2-piperidones from substituted acyclic amides via olefin metathesis, see: (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
33. (c) Garro-Hélion, F.; Guibé, F. Chem. Commun. 1996, 641.
34. (d) Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65.
35. (e) Arisawa, M.; Takezawa, E.; Nishida, A.; Mori, M.; Nakagawa, M. Synlett 1997, 1179. Campagne, J.-M.; Ghosez, L. Tetrahedron Lett. 1998, 39, 6175.
36. (e) Arisawa, M.; Takezawa, E.; Nishida, A.; Mori, M.; Nakagawa, M. Synlett 1997, 1179. Campagne, J.-M.; Ghosez, L. Tetrahedron Lett. 1998, 39, 6175.
37. Propiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inghs, G. G. A. J. Org. Chem. 1998, 63, 2342.
38. (a) For related enzymatic resolutions, see Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914.
39. (b) Sakagami, H.; Ogasawara, K. Synthesis 2000, 521.
40. Lipases AK, PS and R are from Amano; porcine pancreas lipase (PPL) is from Sigma.
41. Conversion measured by proton NMR.
42. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
43. Enantiopurity of (S)- and (R)-2 was measured by chiral column HPLC (Daicel Chiracel AD, see Supporting Information for details).
44. Enantiopurity of (R)-7 was determined by HPLC after its transformation into (R)-2.
45. D - 12.1 (c 2.0. MeOH). see ref 4}.
46. For other syntheses of (S)-9, see (b) Herdeis, C.; Heller, E. Tetrahedron: Asymmetry 1993, 4, 2085.
47. (c) Reddy, P. N.; Han, S.-S.; Chung, K.-H. Bull. Korean Chem. Soc. 1998, 19, 617.