Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 704-712

  Bélanger, Guillaume ^a   Larouche Gauthier, Robin ^a   Ménard, Frédéric ^a   Nantel, Miguel ^a,b   Barabé, Francis ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b MDS Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ETHERS; SILANES; SOLUTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

IMINIUM IONS; NUCLEOPHILES; POLYCYCLIC ALKALOIDS; VILSMEIER-HAACK TYPE CYCLIZATIONS;

AMINES;

ALKALOID; ALLYLSILANE DERIVATIVE; AMIDE; AROMATIC COMPOUND; ENAMINE; ETHER DERIVATIVE; FORMAMIDE DERIVATIVE; IMINE; INDOLE DERIVATIVE; LACTAM; MAAEKIA TASHIROI EXTRACT; NATURAL PRODUCT; POLYCYCLIC AROMATIC COMPOUND; SILANE DERIVATIVE; SILYL ENOL ETHER DERIVATIVE; TASHIROMINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMOSENSITIVITY; CYCLIZATION; MOLECULAR DYNAMICS; NONHUMAN; NUCLEOPHILE; PRODUCT RECOVERY; SPECIES IDENTIFICATION; SYNTHESIS; VILSMEIER HAACK REACTION;

ALKALOIDS; AMIDES; INDOLIZINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 30744440409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052141v     Document Type: Article

References (53)

1. (a) Iminium Salts in Organic Chemistry; Böhme, H., Viehe, H. G., Eds.; Wiley: New York, 1976, part I; 1979, part 2.
2. (b) Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Heathcock, C. H., Eds; Pergamon: Oxford, UK, 1991; Vol. 2, p 1007.
3. (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
4. (b) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
5. For various amide activation conditions, see: (a) Nishiyama, H.; Nagase, H.; Ohno, K. Tetrahedron Lett. 1979, 48, 4671.
6. (b) Keck, G. E.; McLaws, M. D.; Wager, T. T. Tetrahedron 2000, 56, 9875.
7. See also references cited in: (c) Kuhnert, N.; Clemens, I.; Walsh, R. Org. Biomol. Chem. 2005, 3, 1694.
8. (d) Smith, D. C.; Lee, S. W.; Fuchs, P. L. J. Org. Chem. 1994, 59, 348.
9. For addition of heteroatomic nucleophiles to activated amides, see: (a) Charette, A. B.; Chua, P. Synlett 1998, 163.
10. (b) Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499.
11. (c) Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908.
12. (d) Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
13. (e) Sforza, S.; Dossena, A.; Corradini, R.; Virgili, E.; Marchelli, R. Tetrahedron Lett. 1998, 39, 711.
14. (f) Thomas, E. W. Synthesis 1993, 767
15. For selected examples, see: (a) Jackson, A. H.; Shannon, P. V. R.; Wilkins, D. J. Tetrahedron Lett. 1987, 28, 4901.
16. (b) He, F.; Bo, Y.; Altom, D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 6771.
17. Typically the Bischler-Napieralski cyclization: Bischler, A.; Napieralski, B. Chem. Ber. 1893, 26, 903.
18. (a) Marson, C. M. Tetrahedron 1992, 48, 3659.
19. (b) Martinez, A. G.; Alvarez, R. M.; Barcina, J. O.; Cerero, S. M.; Vilar, E. T.; Fraile, A. G.; Hanack, M.; Subramanian, L. R. J. Chem. Soc., Chem. Commun. 1990, 1571.
20. Bélanger, G.; Larouche-Gauthier, R.; Ménard, F.; Nantel, M.; Barabé, F. Org. Lett. 2005, 7, 4431.
21. Enaminones are particularly interesting and versatile intermediates used for natural product synthesis. See: Michael, J. P.; de Koning, C. B.; Gravestock, D.; Hosken, G. D.; Howard, A. S.; Jungmann, C. M.; Krause, R. W. M.; Parsons, A. S.; Pelly, S. C.; Stanbury, T. V. Pure Appl. Chem. 1999, 71, 979.
22. 4 as catalyst for enolate alkylations, see: Gelin, J.; Mortier, J.; Moyroud, J.; Chene, A. J. Org. Chem. 1993, 58, 3473.
23. We also tried the same sequence of reactions but starting with N-methylindole instead of N-Boc-indole. It turns out that the bromo derivative was too unstable and could not be purified before the nucleophilic displacement with the acetamide copper enolate.
24. The use of exo and endo in this paper refers to the amide portion of the substratres. For a more appropriate description of cationic cyclizations involving π-nucleophiles, see: (a) Ben-Ishai, D. J. Chem. Soc., Chem. Commun. 1980, 687.
25. (b) Lochead, A. W.; Proctor, G. R.; Caton, M. P. J. Chem. Soc., Perkin Trans. 1 1984, 2477.
26. Taber, D. F.; Teng, D. J. Org. Chem. 2002, 67, 1607.
27. Huang, P.-Q.; Zheng, X.; Deng, X.-M. Tetrahedron Lett. 2001, 42, 9039.
28. This enamine was unstable, as aldehydic enamines usually are, and had to be used without further purification in the cyclization step. Only the trans enamine was formed.
29. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066.
30. Fleming, I.; Paterson, I. Synthesis 1979, 446.
31. Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
32. Fall, Y.; Vidal, B.; Alonso, D.; Gómez, G. Tetrahedron Lett. 2003, 44, 4467.
33. For this screening, the base used was either 2,6-di-tert-butyl-4- methylpyridine or diisopropylethylamine. This is not critical, since entries 6 10 of Table I gave essentially the same cyclization yield for both of these bases.
34. 2O is added to the solution of 37 and 4-(N,N-dimethylamino)pyridine.
35. 1H NMR spectra of aliquots of the reaction.
36. Nantel, M. M.Sc. Thesis, Université de Sherbrooke, 2004,183 pages.
37. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.
38. (a) For allylsilanes, the yields are reported for their cyclization and reduction. Attempts to hydrolyze the β,γ-unsaturated iminium ion (such as 5, Scheme 1) after cyclization gave inseparable mixtures of α,β- and β,γ-enones. The reduction of the same iminium was also a lot cleaner than the hydrolysis.
39. (b) For silyl enol ethers, the yields are reported for their cyclization and hydrolysis.
40. (c) For aldehydic enamines, which are unstable and could not be isolated, the yields are reported for their formation and cyclization. Hydrolysis of the resulting vinylogous amidinium ions (such as 4, Scheme 2) was not necessary because they were easily isolated and characterized.
41. 1H NMR spectroscopy prior to hydrolysis (see the Supporting Information).
42. Charette, A. B.; Chua, C. Tetrahedron Lett. 1998, 39, 245.
43. Ohmiya, S.; Kubo, H.; Otomasu, H.; Saito, K.; Murakoshi, I. Heterocycles 1990, 30, 537.
44. (a) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Org. Chem. 1990, 55, 1148.
45. (b) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
46. (c) Gage, J. L.; Branchaud, B. P. Tetrahedron Lett. 1997, 38, 7007.
47. (d) David, O.; Blot, J.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Haviari, G.; Célérier, J.-P.; Lhommet, G.; Gramain, J.-C.; Gardette, D. J. Org. Chem. 1999, 64, 3122.
48. (e) Kim, S.-H.; Kim, S.-I.; Lai, S.; Cha, J. K. J. Org. Chem. 1999, 64, 6771.
49. (f) Banwell, M. G.; Beck, D. A. S.; Smith, J. A. Org. Biomol. Chem. 2004, 2, 157.
50. Paulvannan, K.; Schwarz, J. B.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215.
51. The characterization is identical with the one reported for the same compound, but prepared through another route. See: (a) Bergman, J.; Baeckvall, J. E. Tetrahedron 1975, 31, 2063.
52. (b) Gardette, D.; Gramain, J. C.; Lepage, M. E.; Troin, Y. Can. J. Chem. 1989, 67, 213.
53. Ratios were determined from the characteristic signal for the protons α to the amide carbonyl of 14 and 58 appealing at 2.18 ppm (4H) versus the overlapping multiplets at 1.7-1.6 ppm accounting for a total of 6H (4H, β and γ to the amide carbonyl, in 15, and 2H β to the amide carbonyl in 58).