A concise benzotriazolyl-mediated synthesis of 9-methoxycepharanone A

Tetrahedron

Volumn 61, Issue 3, 2005, Pages 665-671

  Rys, Véronique ^a   Couture, Axel ^a   Deniau, Eric ^a   Lebrun, Stéphane ^a   Grandclaudon, Pierre ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

Alkaloids; Aristolactams; Benzotriazole; Isoindolinones

Indexed keywords

9 METHOXYCEPHARANONE A; ARISTOLOLACTAM; BENZOTRIAZOLE DERIVATIVE; FUNCTIONAL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 10044247273     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.079     Document Type: Article

References (44)

1. M. Shamma The Isoquinoline Alkaloids, Chemistry and Pharmacology Vol. 25 1972 Academic New York p 574
2. M. Shamma, and J.L. Moniot Isoquinoline Alkaloids Research, 1972-77 1978 Plenum New York
3. H. Guinaudeau, M. Leboeuf, and A. Cavé J. Nat. Prod. 51 1988 389 474
4. A. Cavé, M. Leboeuf, and B.K. Cassels A. Brossi The Alkaloids Vol. 35 1989 Academic New York 1 74
5. T. Kametani J. Apsimon The Total Synthesis of Natural Products 1977 Wiley Interscience New York 1 272
6. L. Castedo, and G. Tojo A. Brossi The Alkaloids Vol. 39 1990 Academic New York 99 138
7. Z.-L. Chen, and D.-Y. Zhu A. Brossi The Alkaloids Vol. 31 1987 Academic New York 29 65
8. D.S. Han, B.S. Chung, H.J. Chi, and H.S. Lee Korean J. Pharmacogn. (Saengyak Hakhoechi) 20 1989 1 5
9. H.S. Lee, D.S. Han, and D.K. Won Korean J. Pharmacogn. (Saengyak Hakhoechi) 21 1990 52 55
10. P.H. Daves Flora of Turkey and East Aegean Islands Vol. 7 1965 Edinburgh University Press Edinburgh p 551
11. P.J. Houghton, and M. Ogutveren Phytochemistry 30 1991 253 254
12. W.S. Kan Pharmaceutical Botany; National Research Institute of Chinese Medicine 1979 Academic Taiwan p 247
13. H.H. Schmeiser, C.A. Bieler, M. Wiessler, C. Van Ypersele de Strihou, and J.P. Cosyns Cancer Res. 56 1996 2025 2028
14. J.C. Estevez, M.C. Villaverde, R.J. Estevez, and L. Castedo Tetrahedron Lett. 33 1992 5145 5146
15. L. Castedo, E. Guitian, J.M. Saa, and R. Suau Heterocycles 19 1982 279 280
16. L. Castedo, E. Guitian, J.M. Saa, and R. Suau Tetrahedron Lett. 23 1982 457 458
17. N. Atanes, L. Castedo, E. Guitian, C. Saa, J.M. Saa, and R. Suau J. Org. Chem. 56 1991 2984 2988
18. J.C. Estevez, R.J. Estevez, and L. Castedo Tetrahedron 51 1995 10801 10810
19. J.C. Estevez, R.J. Estevez, E. Guitian, M.C. Villaverde, and L. Castedo Tetrahedron Lett. 30 1989 5785 5786
20. A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau J. Org. Chem. 63 1998 3128 3132
21. V. Rys, A. Couture, E. Deniau, and P. Grandclaudon Eur. J. Org. Chem. 2003 1231 1237
22. See also: (a) P. Gorecki, and H. Otta Pharmazie 30 1975 337 338
23. J. Kunimoto, Y. Murakami, and M. Akasu J. Pharm. Soc. Jpn 100 1980 337 341
24. J. Kunimoto, Y. Murakami, M. Oshikata, T. Shingu, M. Akazu, S.T. Lu, and I.S. Chen Phytochemistry 19 1980 2735 2739
25. R. Crohare, H.A. Priestap, M. Farina, M. Cedola, and E.A. Ruveda Phytochemistry 13 1974 1957 1962
26. Y.-C. Chia, F.-R. Chang, C.-M. Teng, and Y.-C. Wu J. Nat. Prod. 63 2000 1160 1163
27. A. Couture, E. Deniau, P. Woisel, and P. Grandclaudon Synthesis 1997 1439 1445
28. C. Hoarau, A. Couture, E. Deniau, and P. Grandclaudon Synthesis 2000 655 660
29. A. Moreau, A. Couture, E. Deniau, and P. Grandclaudon J. Org. Chem. 69 2004 4527 4530
30. A. Couture, E. Deniau, and P. Grandclaudon Tetrahedron 53 1997 10313 10330
31. A.R. Katritzky, X. Lan, J.Z. Yang, and O.V. Denisko Chem. Rev. 98 1998 409 548
32. A.R. Katritzky, Z. Yang, and J.N. Lam J. Org. Chem. 56 1991 6917 6923
33. A.R. Katritzky, and M. Qi Tetrahedron 54 1998 2647 2668
34. A.R. Katritzky, M. Qi, D. Feng, and D.A. Nichols J. Org. Chem. 62 1997 4121 4124
35. A.R. Katritzky, A.V. Ignatchenko, and H. Lang J. Org. Chem. 60 1995 4002 4005
36. A.R. Katritzky, A.V. Ignatchenko, and H. Lang Synth. Commun. 25 1995 1197 1204
37. E. Deniau, and D. Enders Tetrahedron Lett. 43 2002 8055 8058
38. P. Beak, and V. Snieckus Acc. Chem. Res. 15 1982 306
39. V. Snieckus Chem. Rev. 90 1990 879 933
40. A. Reitz, M.A. Avery, M.S. Verlander, and M. Goodman J. Org. Chem. 46 1981 4859 4863
41. S.M. Gadekar, and A.M. Kotsen J. Heterocycl. Chem. 5 1968 129 131
42. A.I. Meyers, J.R. Flisak, and R.A. Aitken J. Am. Chem. Soc. 109 1987 5446 5452
43. E. Brown, J.-P. Robin, and R. Dahl Tetrahedron 38 1982 2569 2579
44. L.F. Fieser, and M. Fieser Reagents for Organic Synthesis Vol. 1 1967 Wiley New York pp 142-144