π-face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides

Tetrahedron Letters

Volumn 44, Issue 12, 2003, Pages 2587-2591

  Wardrop, Duncan J ^a   Burge, Matthew S ^a   Zhang, Wenming ^a   Ortíz, José A ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AMIDE; LACTAM DERIVATIVE; PHENYLIODINE BIS(TRIFLUOROACETATE); PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AZASPIROCYCLIZATION; CHEMICAL REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037450947     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00227-2     Document Type: Article

References (46)

1. For recent reviews of phenolic oxidation, see: (a) Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273; (b) Moriarty, R. M.; Prakash, O. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2001; Vol. 57, p. 327.
2. For recent reviews of phenolic oxidation, see: (a) Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273; (b) Moriarty, R. M.; Prakash, O. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2001; Vol. 57, p. 327.
3. Braun N.A., Ousmer M., Bray J.D., Bouchu D., Peters K., Peters E.M., Ciufolini M.A. J. Org. Chem. 65:2000;4397.
4. Mander L.N. Chem. Rev. 92:1992;573.
5. Iwata C., Murakami K., Okuda O., Morie T., Maezaki N., Yamashita H., Kuroda T., Imanishi T., Tanaka T. Chem. Pharm. Bull. 41:1993;1900.
6. Kusama H., Yamashita Y., Uchiyama K., Narasaka K. Bull. Chem. Soc. Jpn. 70:1997;965.
7. Hashmi A.S.K., Schwartz L., Bolte M. Tetrahedron Lett. 39:1998;8969.
8. Murphy W.S., Wattanasin S. Chem Soc. Rev. 12:1983;213.
9. Hobbs-Mallyon D., Li W., Whiting D.A. J. Chem. Soc., Perkin Trans. 1. 1997;1511.
10. For a case in point, see: Bell V.L., Giddings P.J., Holmes A.B., Mock G.A., Raphael R.A. J. Chem. Soc., Perkin Trans. 1. 1986;1515.
11. Glover S.A., Goosen A., McCleland C.W., Schoonraad J.L. J. Chem. Soc., Perkin Trans. 1. 1984;2255.
12. Kawase M., Kitamura T., Kikugawa Y. J. Org. Chem. 54:1989;3394.
13. Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. PCT Int. Appl. 1991, WO 9,113,887 (TAN1251) Blackman, A. J.; Li, C. P.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645 (Cylindricine-A) Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691 (Lepadiformine) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37 (FR901483) Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Tetrahedron Lett. 1997, 38, 363 (Fasicularin).
14. For example, see: Fujimoto R.A., Boxer J., Jackson R.H., Simke J.P., Neale R.F., Snowhill E.W., Barbaz B.J., Williams M., Sills M.A. J. Med. Chem. 32:1989;1259.
15. Wardrop D.J., Basak A. Org. Lett. 3:2001;1053.
16. Wardrop D.J., Zhang W. Org. Lett. 3:2001;2353.
17. For recent reviews, see: (a) Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron: Asymmetry 1996, 7, 317; (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729; (c) Harman, W. D. Chem. Rev. 1997, 97, 1953; (d) Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917.
18. For recent reviews, see: (a) Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron: Asymmetry 1996, 7, 317; (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729; (c) Harman, W. D. Chem. Rev. 1997, 97, 1953; (d) Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917.
19. For recent reviews, see: (a) Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron: Asymmetry 1996, 7, 317; (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729; (c) Harman, W. D. Chem. Rev. 1997, 97, 1953; (d) Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917.
20. For recent reviews, see: (a) Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron: Asymmetry 1996, 7, 317; (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729; (c) Harman, W. D. Chem. Rev. 1997, 97, 1953; (d) Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917.
21. Mislow K., Siegel J. J. Am. Chem. Soc. 106:1984;3319.
22. For reports where π-facial selectivity is observed during the oxidative spirocyclization of phenols, see: (a) Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1978; (b) Murakata, M.; Tamura, M.; Hoshino, O. J. Org. Chem. 1997, 62, 4428; (c) Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549; (d) Drutu, I.; Njardarson, J.; Wood, J. L. Org. Lett. 2002, 4, 493; (e) Plourde, G. L. Tetrahedron Lett. 2002, 43, 3597.
23. For reports where π-facial selectivity is observed during the oxidative spirocyclization of phenols, see: (a) Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1978; (b) Murakata, M.; Tamura, M.; Hoshino, O. J. Org. Chem. 1997, 62, 4428; (c) Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549; (d) Drutu, I.; Njardarson, J.; Wood, J. L. Org. Lett. 2002, 4, 493; (e) Plourde, G. L. Tetrahedron Lett. 2002, 43, 3597.
24. For reports where π-facial selectivity is observed during the oxidative spirocyclization of phenols, see: (a) Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1978; (b) Murakata, M.; Tamura, M.; Hoshino, O. J. Org. Chem. 1997, 62, 4428; (c) Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549; (d) Drutu, I.; Njardarson, J.; Wood, J. L. Org. Lett. 2002, 4, 493; (e) Plourde, G. L. Tetrahedron Lett. 2002, 43, 3597.
25. For reports where π-facial selectivity is observed during the oxidative spirocyclization of phenols, see: (a) Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1978; (b) Murakata, M.; Tamura, M.; Hoshino, O. J. Org. Chem. 1997, 62, 4428; (c) Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549; (d) Drutu, I.; Njardarson, J.; Wood, J. L. Org. Lett. 2002, 4, 493; (e) Plourde, G. L. Tetrahedron Lett. 2002, 43, 3597.
26. For reports where π-facial selectivity is observed during the oxidative spirocyclization of phenols, see: (a) Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1978; (b) Murakata, M.; Tamura, M.; Hoshino, O. J. Org. Chem. 1997, 62, 4428; (c) Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549; (d) Drutu, I.; Njardarson, J.; Wood, J. L. Org. Lett. 2002, 4, 493; (e) Plourde, G. L. Tetrahedron Lett. 2002, 43, 3597.
27. Atkinson R.S., Gawad N.A. J. Chem. Soc., Perkin Trans. 1. 1985;335.
28. The preparation of cyclization substrates 7a-l, 9a, 9b, and 12 will be reported elsewhere.
29. 2=0.2398 for all data. Crystallographic data (excluding structure factors) for the structure in this paper, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 201039.
30. 4), filtered, concentrated under reduced pressure, and the residue purified by radial chromatography on silica gel (2 mm, EtOAc/hexanes, 1:1) to provide anti-8a (35 mg, 75% yield) as white crystals.
31. Hoffmann R.W. Chem. Rev. 89:1989;1841.
32. Analogous rationalizations of π-facial diastereoselectivity are proposed in: (a) Wender, P. A.; Ternansky, R. J. Tetrahedron Lett. 1985, 26, 2625; (b) Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686; (c) Kamikawa, K.; Furusyo, M.; Uno, T.; Sato, Y.; Konoo, A.; Bringmann, G.; Uemura, M. Org. Lett. 2001, 3, 3667.
33. Analogous rationalizations of π-facial diastereoselectivity are proposed in: (a) Wender, P. A.; Ternansky, R. J. Tetrahedron Lett. 1985, 26, 2625; (b) Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686; (c) Kamikawa, K.; Furusyo, M.; Uno, T.; Sato, Y.; Konoo, A.; Bringmann, G.; Uemura, M. Org. Lett. 2001, 3, 3667.
34. Analogous rationalizations of π-facial diastereoselectivity are proposed in: (a) Wender, P. A.; Ternansky, R. J. Tetrahedron Lett. 1985, 26, 2625; (b) Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686; (c) Kamikawa, K.; Furusyo, M.; Uno, T.; Sato, Y.; Konoo, A.; Bringmann, G.; Uemura, M. Org. Lett. 2001, 3, 3667.
35. Fischer A., Henderson G.N., Iyer L.M. Can. J. Chem. 63:1985;2390.
36. 23 rapidly undergo Diels-Alder dimerization and consequently cannot be isolated. In our case, this pathway may be less favorable since the N-methoxyl group effectively blocks the adjoining π-system from attack.
37. Kacan M., Koyuncu D., McKillop A. J. Chem. Soc., Perkin Trans. 1. 1993;1771.
38. For recent approaches to 1-azaspiro[5.5]undecanes, see: (a) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109; (b) Stockmann, R. A. Tetrahedron Lett. 2000, 41, 9163; (c) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864; (d) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485; (e) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
39. For recent approaches to 1-azaspiro[5.5]undecanes, see: (a) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109; (b) Stockmann, R. A. Tetrahedron Lett. 2000, 41, 9163; (c) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864; (d) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485; (e) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
40. For recent approaches to 1-azaspiro[5.5]undecanes, see: (a) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109; (b) Stockmann, R. A. Tetrahedron Lett. 2000, 41, 9163; (c) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864; (d) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485; (e) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
41. For recent approaches to 1-azaspiro[5.5]undecanes, see: (a) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109; (b) Stockmann, R. A. Tetrahedron Lett. 2000, 41, 9163; (c) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864; (d) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485; (e) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
42. For recent approaches to 1-azaspiro[5.5]undecanes, see: (a) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109; (b) Stockmann, R. A. Tetrahedron Lett. 2000, 41, 9163; (c) Kim, D.; Shim, P. J.; Lee, J.; Park, C. W.; Hong, S. W.; Kim, S. J. Org. Chem. 2000, 65, 4864; (d) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485; (e) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
43. Comins D.L., Zhang Y.M., Zheng X.L. Chem. Commun. 1998;2509.
44. Williams G.M., Roughley S.D., Davies J.E., Holmes A.B., Adams J.P. J. Am. Chem. Soc. 121:1999;4900.
45. Abe H., Aoyagi S., Kibayashi C. J. Am. Chem. Soc. 122:2000;4583.
46. Maeng J.-H., Funk R.L. Org. Lett. 4:2002;331.