Asymmetric synthesis of alkaloid (-)-(2S,4S) SS 20846 A and its C-4 epimer

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1998, Pages 3485-3492

  Ripoche, Isabelle ^a   Canet, Jean Louis ^a   Aboab, Bettina ^b   Gelas, Jacques ^a   Troin, Yves ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b UMR 6504   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748480356     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804288h     Document Type: Article

References (49)

1. H. M. Garrafo, J. Caceres, J. W. Daly and T. F. Spande, J. Nat. Prod., 1993, 56, 1016.
2. P. D. Bailey, P. A. Millwood and P. D. Smith, Chem. Commun., 1998, 633.
3. (a) For a monograph on 4-piperidone chemistry see: M. Rubiralta, E. Giralt and A. Diez, Piperidine Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and its Derivatives, Elsevier, Amsterdam, 1991;
4. (b) M. Rubiralta, A. Diez, C. Vila, Y. Troin and M. Feliz, J. Org. Chem., 1991, 56, 6292;
5. (c) D. L. Comins and D. H. Lamunyon, J. Org. Chem., 1992, 57, 5807;
6. (d) A. Diez, S. Mavel, J. C. Teulade, O. Chavignon, M. E. Sinibaldi, Y. Troin and M. Rubiralta, Heterocycles, 1993, 36, 2451.
7. L. V. Kudzma, S. A. Severnak, M. J. Benvenga, E. F. Ezell, M. H. Ossipov, V. V. Knight, F. G. Rudo, H. K. Spencer and T. C. Spaulding, J. Med. Chem., 1989, 32, 2534 and references cited therein.
8. (a) M. E. Kuehne, P. A. Matson and W. G. Bornmann, J. Org. Chem., 1991, 56, 513;
9. (b) M. Rubiralta, A. Diez, C. Vila, J. Castells and I. Lopez, Heterocycles, 1992, 34, 643.
10. J. Barluenga, F. Aznar, C. Ribas, C. Valdés, M. Fernandez, M. P. Cabal and J. Trujillo, Chem. Eur. J., 1996, 2, 805 and references cited therein.
11. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Book, Mill Valley, CA, 1994.
12. (a) A. J. Pearson, Iron Compounds in Organic Synthesis, Academic Press, London, 1994;
13. (b) R. Grée and J. P. Lellouche, Advances in Metal Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, CT, 1995, vol. 4.
14. (a) E. Wenkert, K. G. Dave and R. V. Stevens, J. Am. Chem. Soc., 1968, 90, 6177;
15. (b) this cyclization process has been successfully applied in the alkaloid field, see ref. 1a.
16. I. Ripoche, J. Gelas, D. Grée, R. Grée and Y. Troin, Tetrahedron Lett., 1995, 36, 6675.
17. A. Monpert, J. Martelli, R. Grée and R. Carrié, Tetrahedron Lett., 1981, 22, 1961.
18. C. H. Heathcock, S. W. Davidsen, S. G. Mills and M. A. Sanner, J. Org. Chem., 1992, 57, 2531.
19. The Ψ endo and Ψ exo nomenclature was introduced by N. A. Clinton and C. P. Lillya, J. Am. Chem. Soc., 1970, 92, 3058.
20. This TLC method has been extensively used and has proven itself to be very reliable, see: A. Teniou, L. Toupet and R. Grée, Synlett, 1991, 195 and references cited therein.
21. R. Grée, Synthesis, 1989, 341.
22. H.J. Knökler, M. Bauermeister and J. B. Pannek, Tetrahedron, 1993, 49, 841.
23. Since our preliminary report, extensive studies on the use of MTPA amides for the assignment of amine configuration have been published: see T. R. Hoye and M. K. Renner, J. Org. Chem., 1996, 61, 2056 and 8489.
24. Optical purity was checked by chiral capillary electrophoresis, see: P. Baumy, P. Morin, M. Dreux, M. C. Viaud, S. Boye and G. Guillaumet, J. Chromatogr. A, 1995, 707, 311.
25. For a previous synthesis of alkaloid (-)-6 see: (a) Y. Takemoto, S. Ueda, J. Takeuchi, Y Baba and C. Iwata, Chem. Pharm. Bull., 1997, 45, 1906;
26. (b) Y. Takemoto, S. Ueda, J. Takeuchi, T. Nakamoto and C. Iwata, Tetrahedron Lett., 1994, 35, 8821.
27. M. Mayer and R. Thiericke, J. Org. Chem., 1993, 58, 3486;
28. S. Grabley, P. Hammann, H. Kluge, J. Wink, P. Kricke and A. Zeeck, J. Antibiot., 1991, 44, 797.
29. T. Komoto, K. Yano, J. Ono, J. Okawa and T. Nakajima, Jpn. Kokai, 35788 (20/02/1986) (Chem. Abstr., 1986, 105, 132 137w).
30. A lot of complexes has been resolved by several methods including fractional recrystallization or chromatographic separation of preformed diastereomers: for leading references see: (a) J. Howell, M. Palin, P. O'Leary, S. Top and G. Jaouen, Tetrahedron: Asymmetry, 1996, 7, 307;
31. (b) S. Nakanishi, K. Kumeta, J. I. Nakanishi and T. Takata, Tetrahedron: Asymmetry, 1995, 9, 2097;
32. (c) M. Franck-Neumann, C. Briswalter, P. Chemla and D. Martina, Synlett, 1990, 637;
33. (d) D. Cuvinot, P. Mangeney, A. Alexakis, J. F. Normant and J. P. Lellouche, J. Org. Chem., 1989, 54, 2420.
34. J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis, Wiley VCH, New York, 1997 and references cited therein.
35. A. Diez, M. Tona and M. Rubiralta, Tetrahedron, 1991, 46, 4396.
36. A multistep procedure involving transacetalization of the dioxolane to a dithiane and subsequent deprotection has been proposed, see: I. Lopez, A. Diez and M. Rubiralta, Tetrahedron, 1996, 52, 8581.
37. Retro Michael ring opening leading to the corresponding enones has been observed in some cases. These enones usually recyclize spontaneously to regenerate piperidones but this mechanism leads to racemization at the C-2 position, see: M. Rubiralta, A. Diez, C. Vila, J. L. Bettiol, Y. Troin and M. E. Sinibaldi, Tetrahedron Lett., 1992, 33, 1233.
38. T. W. Greene and P. G. M. Wuts, in Protective Groups in Organic Synthesis, Wiley Interscience, New York, 2nd edn., 1991.
39. (a) M. Uemura, T. Minami and Y. Hayashi, Tetrahedron Lett., 1988, 29, 6271;
40. (b) B. Lipshutz, D. Pollart, G. Montforte and H. Kotsuki, Tetrahedron Lett., 1985, 26, 705;
41. (c) P. Beak and W. K. Lee, J. Org. Chem., 1993, 58, 1109.
42. R. W. Hoffmann, Chem. Rev. (Washington, D.C.), 1989, 89, 1841.
43. (a) P. Beak and W. J. Zadjel, J. Am. Chem. Soc., 1984, 106, 1010;
44. (b) J. D. Brown, M. A. Foley and D. L. Comins, J. Am. Chem. Soc., 1988, 110, 7445.
45. W. C. Still, Macromodel/Batchmin Molecular Modeling package, ver. 5.0, Columbia University, New York, 1995.
46. MOPAC, ver. 6.0, QCPE no 455, Department of Chemistry, Indiana University, 1990.
47. P. Morin, D. Bellesort, M. Dreux, Y. Troin and J. Gelas, J. Chromatogr. A, 1998, 796, 375.
48. J. A. S. Howell, M. G. Palin, G. Jaouen, S. Top, H. El Hafa and J. Cense, Tetrahedron: Asymmetry, 1993, 4, 1241.
49. J. E. Mahler and R. Pettit, J. Am. Chem. Soc., 1963, 85, 3955.