Synthesis of fused bicyclic glutarimides

Tetrahedron

Volumn 59, Issue 38, 2003, Pages 7547-7553

  Chang, Meng Yang ^a   Chen, Chung Yi ^b   Chen, Shui Tein ^c   Chang, Nein Chen ^b  

^a NATIONAL UNIVERSITY OF KAOHSIUNG   (Taiwan)

^b NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^c INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

Bicyclic glutarimides; Intramolecular alkylation; Oxidative cyclization or ring closing metathesis; Stepwise 3+3 annulation

Indexed keywords

1 ALLYL 2 (4 METHYLPHENYLSULFONYL)ACETAMIDE; 1 ALLYL 3 (4 METHYLPHENYLSULFONYL) 4 (1 BUTENYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (3 BENZYLOXYPROPYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (3 CHLOROPROPYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (3 HYDROXYPROPYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (3 METHANE SULFONYLPROPYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (4 BENZYLOXYBUTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (4 CHLOROBUTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (4 HYDROXYBUTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (4 METHANE SULFONYLBUTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (5 BENZYLOXYPENTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (5 CHLOROPENTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (5 HYDROXYPENTYL)PIPERIDINE 2,6 DIONE; 1 BENZYL 3 (4 METHYLPHENYLSULFONYL) 4 (5 METHANE SULFONYLPENTYL)PIPERIDINE 2,6 DIONE; 1 [2 (3 INDOLYL)ETHYL] 3 (4 METHYLPHENYLSULFONYL) 4 (4 BENZYLOXYBUTYL)PIPERIDINE 2,6 DIONE; 1 [2 (3 INDOLYL)ETHYL] 3 (4 METHYLPHENYLSULFONYL) 4 (4 HYDROXYBUTYL)PIPERIDINE 2,6 DIONE; 1 [2 (3 INDOLYL)ETHYL] 3 (4 METHYLPHENYLSULFONYL) 4 METHANESULFONYLBUTYL)PIPERIDINE 2,6 DIONE; 2 ALLYL 9A (4 METHYLPHENYLSULFONYL) 4,4A,5,8,9,9A HEXAHYDROCYCLOHEPTA[C]PYRIDINE 1,3 DIONE; 2 BENZYL 7 HYDROXY 7A (4 METHYLPHENYLSULFONYL)HEXAHYDRO[2]PYRIDINE 1,3 DIONE; 2 BENZYL 7A (4 METHYLPHENYLSULFONYL)HEXAHYDRO[2]PYRIDINE 1,3 DIONE; 2 BENZYL 8 HYDROXY 8A (4 METHYLPHENYLSULFONYL)HEXAHYDRO[2]PYRIDINE 1,3 DIONE; 2 BENZYL 8A (4 METHYLPHENYLSULFONYL)HEXAHYDROISOQUINOLINE 1,3 DIONE; 2 [2 (3 INDOLYL)ETHYL] 8A (4 METHYLPHENYLSULFONYL)HEXAHYDROISOQUINOLINE 1,3 DIONE; ACETAMIDE DERIVATIVE; ESTER DERIVATIVE; GLUTARIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0042330507     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01198-0     Document Type: Article

References (46)

1. (a) Dawson N., Figg W.D., Brawley O.W., Bergan R., Cooper M.R., Reed E., Sartor O. Chin. Cancer Res. 4:1998;37
2. (b) Moreia A.L., Corral L.G., Ye W., Johnson B.A., Stirling D., Muller G.W., Freedman V.H., Kaplan G. AIDS Res. Hum. Retoviruses. 13:1997;857
3. (c) Waelbroeck M., Lazareno S., Plaff O., Friebe T., Tastoi M., Mutschler E., Lambert G. Br. J. Pharmacol. 119:1996;1319
4. (d) Park M., Lee J., Choi J. Bioorg. Med. Chem. Lett. 6:1996;1297.
5. (a) Kiyota H., Shimizu Y., Oritani T. Tetrahedron Lett. 41:2000;5887
6. (b) Bushell S.M., Crump J.P., Lawrence N.J., Pineau G. Tetrahedron. 54:1998;2269
7. (c) Achmatowicz O., Malinowska I., Szechner B., Maurin J.K. Tetrahedron. 53:1997;7917
8. (d) Fadel A., Garciaargote S. Tetrahedron: Asymmetry. 7:1996;1159
9. (e) Kim M.H., Patel D.V. Tetrahedron Lett. 35:1994;5603.
10. (a) Chang M.Y., Chang C.H., Chen S.T., Chang N.C. J. Chin. Chem. Soc. 49:2002;383
11. (b) Nazar F., Pham-Huy C., Galons H. Tetrahedron Lett. 40:1999;3697
12. (c) Zhu J., Pham-Huy C., Lemoine P., Tomas A., Galons H. Heterocycles. 42:1996;1923
13. (d) Robin S., Zhu J., Galons H., Pham-Huy C., Claude J.R., Tomas A., Viossat B. Tetrahedron: Asymmetry. 6:1995;1249
14. (e) Shealy Y., Opliger C.E., Montgomery J.A. J. Pharm. Sci. 57:1968;757
15. (f) Service R.F. Science. 269:1995;1340
16. (g) Chang M.Y., Chang B.R., Tai H.M., Chang N.C. Tetrahedron Lett. 41:2000;10273.
17. (a) Huang C.G., Chang B.R., Chang N.C. Tetrahedron Lett. 43:2002;2721
18. (b) Chang B.R., Chen C.Y., Chang N.C. Tetrahedron Lett. 43:2002;3233
19. (c) Chang M.Y., Chen S.T., Chang N.C. Tetrahedron. 58:2002;3623
20. (d) Chang M.Y., Chen S.T., Chang N.C. Tetrahedron. 58:2002;5075
21. (e) Hsu R.T., Cheng L.M., Chang N.C., Tai H.M. J. Org. Chem. 67:2002;5044
22. (f) Chang M.Y., Chen S.T., Chang N.C. Heterocycles. 57:2002;2321
23. (g) Chang M.Y., Lin J.Y.C., Chen S.T., Chang N.C. J. Chin. Chem. Soc. 49:2002;1079
24. (h) Chang M.Y., Lin J.Y.C., Chen S.T., Chang N.C. J. Chin. Chem. Soc. 49:2002;1015
25. (i) Chang M.Y., Chen S.T., Chang N.C. Heterocycles. 60:2003;99
26. (j) Chang M.Y., Chen S.T., Chang N.C. Synth. Commun. 33:2003;1375.
27. (a) Woodson R.E., Youngken H.W., Schlittler E., Schneider J.A. Rauwolfia: Botany, Pharmacognocy, Chemistry and Pharmacology. 1957;Little Brown and Co, Boston,
28. (b) Baxter E.W., Mariano P.S. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 8:1992;197-319 Spring, New York. Review.
29. (a) Lorvelec G., Vaultier M. Tetrahedron Lett. 39:1998;5185 (b) Mathison I.W., Morgan P.H. J. Med. Chem. 17:1974;1136 (c) Okamoto M. Chem. Pharm. Bull. 15:1967;168. For synthesis: (d) Sparks S.M., Shea K. J. Tetrahedron Lett. 41:2000;6721. and cited references herein.
30. (a) Lorvelec G., Vaultier M. Tetrahedron Lett. 39:1998;5185 (b) Mathison I.W., Morgan P.H. J. Med. Chem. 17:1974;1136 (c) Okamoto M. Chem. Pharm. Bull. 15:1967;168. For synthesis: (d) Sparks S.M., Shea K. J. Tetrahedron Lett. 41:2000;6721. and cited references herein.
31. (a) Lorvelec G., Vaultier M. Tetrahedron Lett. 39:1998;5185 (b) Mathison I.W., Morgan P.H. J. Med. Chem. 17:1974;1136 (c) Okamoto M. Chem. Pharm. Bull. 15:1967;168. For synthesis: (d) Sparks S.M., Shea K. J. Tetrahedron Lett. 41:2000;6721. and cited references herein.
32. (a) Lorvelec G., Vaultier M. Tetrahedron Lett. 39:1998;5185 (b) Mathison I.W., Morgan P.H. J. Med. Chem. 17:1974;1136 (c) Okamoto M. Chem. Pharm. Bull. 15:1967;168. For synthesis: (d) Sparks S.M., Shea K. J. Tetrahedron Lett. 41:2000;6721. and cited references herein.
33. (a) Padwa A., Beall L.S., Heidelbaugh T.M., Liu B., Sheehan S.M. J. Org. Chem. 65:2000;2684
34. (b) Sparks S.M., Shea K. J. Tetrahedron Lett. 41:2000;6721. and cited references herein.
35. For related examples of RCM, see: (a) Rutjes F.P.J.T., Schoemaker H.E. Tetrahedron Lett. 38:1997;677 (b) Liras S., Allen M.P., Blake J.F. Org. Lett. 3:2001;3483 (c) Tarling C.A., Holmes A.B., Markwell R.E., Pearson N.D. J. Chem. Soc., Perkin Trans. 1. 1999;1695 (d) Lim S.H., Ma S., Beak P. J. Org. Chem. 66:2001;9056.
36. For related examples of RCM, see: (a) Rutjes F.P.J.T., Schoemaker H.E. Tetrahedron Lett. 38:1997;677 (b) Liras S., Allen M.P., Blake J.F. Org. Lett. 3:2001;3483 (c) Tarling C.A., Holmes A.B., Markwell R.E., Pearson N.D. J. Chem. Soc., Perkin Trans. 1. 1999;1695 (d) Lim S.H., Ma S., Beak P. J. Org. Chem. 66:2001;9056.
37. For related examples of RCM, see: (a) Rutjes F.P.J.T., Schoemaker H.E. Tetrahedron Lett. 38:1997;677 (b) Liras S., Allen M.P., Blake J.F. Org. Lett. 3:2001;3483 (c) Tarling C.A., Holmes A.B., Markwell R.E., Pearson N.D. J. Chem. Soc., Perkin Trans. 1. 1999;1695 (d) Lim S.H., Ma S., Beak P. J. Org. Chem. 66:2001;9056.
38. For related examples of RCM, see: (a) Rutjes F.P.J.T., Schoemaker H.E. Tetrahedron Lett. 38:1997;677 (b) Liras S., Allen M.P., Blake J.F. Org. Lett. 3:2001;3483 (c) Tarling C.A., Holmes A.B., Markwell R.E., Pearson N.D. J. Chem. Soc., Perkin Trans. 1. 1999;1695 (d) Lim S.H., Ma S., Beak P. J. Org. Chem. 66:2001;9056.
39. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
40. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
41. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
42. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
43. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
44. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
45. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.
46. For reviews of RCM, see: (a) Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446 (b) Schmalz H.G. Angew. Chem. Int. Ed. Engl. 34:1995;1833 (c) Philips A.J., Abell A.D. Aldrichimica Acta. 32:1999;75 (d) Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371 (e) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036 (f) Pandit U.K., Overkleeft H.S., Borer B.C., Bieraugel H. Eur. J. Org. Chem. 5:1999;959 (g) Wright D.L. Curr. Org. Chem. 3:1999;75 (h) Maier M.E. Angew. Chem. Int. Ed. Engl. 39:2000;2073.