New and efficient routes for the synthesis of murrayaquinone A and murrayanine

Tetrahedron

Volumn 68, Issue 32, 2012, Pages 6420-6426

  Bhosale, Shrikar M ^a   Momin, Aadil A ^a   Kusurkar, Radhika S ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

Dakin reaction; Murrayanine; Murrayaquinone A; Sodium cyanoborohydride

Indexed keywords

(9 BENZYL 1,4 DIMETHOXY 9H CARBAZOL 3 YL)METHANOL; 1 BROMO 3 FORMYL 9H CARBAZOL 4 YL TRIFLUOROMETHANESULFONATE; 1 BROMO 4 HYDROXY 9H CARBAZOLE 3 CARBALDEHYDE; 1 BROMO 9H CARBAZOLE 3 CARBALDEHYDE; 1 METHOXY 9H CARBAZOLE 3 CARBALDEHYDE; 3 [(2 IODOPHENYLIMINO)METHYL] 9H CARBAZOL 4 OL; 3 BROMO 4 HYDROXY 9H CARBAZOLE 1 CARBALDEHYDE; 3 METHYL 9H CARBAZOLE 1,4 DIONE; 3 MMETHYL 9H CARBAZOL 4 OL; 4 HYDROXY 9H CARBAZOLE 1 CARBALDEHYDE; 4 HYDROXY 9H CARBAZOLE 3 CARBALDEHYDE; 4 HYDROXY CARBAZOLE; 9 BENZYL (4 BENZYLOXY) 1 BROMO 9H CARBAZOLE 3 CARBALDEHYDE; 9 BENZYL 3 (BROMOMETHYL) 9H CARBAZOLE 1,4 DIONE; 9 BENZYL 3 (HYDROXYMETHYL) 9H CARBAZOLE 1,4 DIONE; 9 BENZYL 3 METHYL 9H CARBAZOLE 1,4 DIONE; 9 BENZYL 4 (BENZOLOXY) 3 BROMO 1 (1,3 DIOXAN 2 YL) 9H CARBAZOLE; 9 BENZYL 4 (BENZYLOXY) 1 (1,3 DIOXAN 2 YL) 3 METHYL 9H CARBAZOLE; 9 BENZYL 4 (BENZYLOXY) 3 BROMO 9H CARBAZOLE 1 CARBALDEHYDE; CARBAZOLE DERIVATIVE; CARDIOTONIC AGENT; CYANOBOROHYDRIDE SODIUM; MURRAYANINE; MURRAYAQUINONE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 84862762757     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.127     Document Type: Article

References (47)

1. T.S. Wu, T. Ohta, H. Furukawa, and C.S. Kuoh Heterocycles 20 1983 1267
2. H. Furukawa, T.S. Wu, T. Ohta, and C.S. Kuoh Chem. Pharm. Bull. 33 1985 4132
3. H. Furukawa J. Indian Chem. Soc. 71 1994 303
4. C.J. Moody Synlett 1994 681
5. Z. Bouaziz, P. Nebois, A. Poumaroux, and H. Fillion Heterocycles 52 2000 977
6. M. Yogo, C. Ito, and H. Furukawa Chem. Pharm. Bull. 39 1991 328
7. K. Takeya, M. Itoigawa, and H. Furukawa Eur. J. Pharmacol. 169 1989 137
8. D.P. Chakraborty G.A. Cordell, The Alkaloids vol. 44 1993 Academic New York, NY 257
9. T. Choshi Yakugaku Zasshi 121 2001 487
10. H.-J. Knölker, and K.R. Reddy Chem. Rev. 102 2002 4303
11. H.-J. Knölker Top. Curr. Chem. 244 2005 115
12. H.-J. Knölker, and K.R. Reddy G.A. Cordell, The Alkaloids vol. 65 2008 Academic Amsterdam 1 430
13. K. Ramesh, and R.S. Kapil Chem. Ind. (London) 1986 614
14. K. Ramesh, and R.S. Kapil J. Nat. Prod. 50 1987 932
15. T. Martin, and C.J. Moody J. Chem. Soc., Perkin Trans. 1 1 1988 235
16. K. Matsuo, and S. Ishida Chem. Express 8 1993 321
17. K. Matsuo, and S. Ishida Chem. Pharm. Bull. 42 1994 1325
18. A. Wada, S. Hirai, and M. Hanaoka Chem. Pharm. Bull. 42 1994 416
19. B. Akermark, J.D. Oslob, and U. Heuschert Tetrahedron Lett. 36 1995 1325
20. Y. Murakami, H. Yokoo, and T. Watanabe Heterocycles 49 1998 127
21. W.S. Murphy, and M. Bertrand J. Chem. Soc., Perkin Trans. 1 1998 4115
22. B.K. Chowdhury, S. Jha, B.R. Kar, and C. Saha Indian J. Chem. Sect B: Org. Chem. Incl. Med. Chem. 38B 1999 1106
23. H. Hagiwara, T. Choshi, H. Fujimoto, E. Sugino, and S. Hibino Chem. Pharm. Bull. 46 1998 1948
24. H. Hagiwara, T. Choshi, J. Nobuhiro, H. Fujimoto, and S. Hibino Chem. Pharm. Bull. 49 2001 881
25. D. Mal, B.K. Senapati, and P. Pahari Tetrahedron 63 2007 3768
26. T. Nishiyama, T. Choshi, K. Kitano, and S. Hibino Tetrahedron Lett. 52 2011 3876
27. D.P. Chakraborty, and S. Roy W. Herz, H. Grisebach, G.W. Kirby, W. Steglich, C. Tamm, Progress in the Chemistry of Organic Natural Products vol 57 1991 springer Wien 71
28. D.P. Chakraborty, B.K. Barman, and P.K. Bose Tetrahedron 21 1965 681
29. P. Bhattacharyya, and D.P. Chakraborty Phytochemistry 12 1973 1831
30. N.M. Cuong, T.Q. Hung, T.V. Sung, and W.C. Taylor Chem. Pharm. Bull. 52 2004 1175
31. K.C. Das, D.P. Chakraborty, and P.K. Bose Experientia 21 1965 340
32. R. Bautista, P. Bernal, L.E. Montiel, F. Delgado, and J. Tamariz Synthesis 6 2011 929
33. P. Bernal, and J. Tamariz Helv. Chim. Acta 9 2007 1449
34. A. Benavides, J. Peralta, F. Delgado, and J. Tamariz Synthesis 2004 2499
35. G. Bringmann, S. Tasler, H. Endress, K. Peters, and E.-M. Peters Synthesis 1998 1501
36. H.-J. Knolker, and M. Bauermeister Chem. Commun. 9 1990 664
37. H.-J. Knolker, and M. Bauermeister Tetrahedron 49 1993 11221
38. H.-J. Knolker K.H. Dötz, R.W. Hoffmann, Organic Synthesis via Organometallics 1991 119
39. H.-J. Knolker Synlett 1992 371
40. H.-J. Knolker C.J. Moody, Advances in Nitrogen Heterocycles vol. 1 1995 JAI Greenwich 173
41. J.D. Crum, and P.W. Sprague J. Chem. Soc., Chem. Commun. 1966 417
42. D.P. Chakraborty, and B.K. Chowdhury J. Org. Chem. 33 1968 1265
43. H.-J. Knolker, and M. Bauermeister J. Chem. Soc., Chem. Commun. 1990 664
44. Y. Miki, and H. Hachiken Synlett 1993 333
45. P.K. Singh, J.K. Koacher, and J.P. Tandon J. Inorg. Nucl. Chem. 43 1981 1751
46. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry 2007 springer Virginia 694 695 Part A
47. S.M. Bhosale, R.L. Gawade, V.G. Puranik, and R.S. Kusurkar Tetrahedron Lett. 53 2012 2854