Concise synthesis of tylophorine

Tetrahedron

Volumn 69, Issue 14, 2013, Pages 2996-3001

  Lin, Qi Xian ^a   Ho, Tse Lok ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Double Suzuki coupling; Phenanthroindolizidine alkaloid; Stevens rearrangement; Symmetry for synthesis design; Tylophorine

Indexed keywords

1 BENZYL 2 [(2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL]PYRROLIDINE; 1 BENZYL 5 ((2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL) 2 PYRROLIDINONE; 1 BENZYL 5 (2 PROPYNYL) 2 PYRROLIDINONE; 1 BENZYL 5 [(2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL] 2 PYRROLIDINONE; 1 BENZYL 5 [3 (4,4',5,5' TETRAMETHOXYBIPHENYL 2 YL) 2 PROPYNYL] 2 PYRROLIDINONE; 1 BENZYL 5 HYDROXY 5 (2 PROPYNYL)PYRROLIDIN 2 ONE; 2 [(2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL]PYRROLIDINE; 5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 1 (2 PROPYNYL) 2 PYRROLIDINONE; 5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 1 [(2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL] 2 PYRROLIDINONE; 5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 1 [3 (3',4,4',5 TETRAMETHOXYBIPHENYL 2 YL)PROP 2 YNYL] 2 PYRROLIDINONE; 5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 2 PYRROLIDINONE; 5 HYDROXYMETHYL 1 [(2,3,6,7 TETRAMETHOXYPHENANTHREN 9 YL)METHYL] 2 PYRROLIDINONE; 9,10 BIS(BROMOMETHYL) 2,3,6,7 TETRAMETHOXYPHENANTHRENE; BIPHENYL DERIVATIVE; PENTACYCLIC HYDROXYLACTAM; PHENANTHRENE DERIVATIVE; PYRROLIDINE DERIVATIVE; TYLOPHORINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEVENS REARRANGEMENT; SUZUKI REACTION;

EID: 84874654169     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.02.014     Document Type: Article

References (45)

1. C. Gopalakrishnan, D. Shankaranarayan, L. Kameswaran, and S. Natarajan Indian J. Med. Res. 69 1979 513 520
2. E. Gellert J. Nat. Prod. 45 1982 50 73
3. A.N. Rathnagiriswaran, and K. Venkatachalam Indian J. Med. Res. 22 1935 433 441
4. Z. Li, Z. Jin, and R. Huang Synthesis 2001 2365 2379
5. D.S. Bhakuni J. Indian Chem. Soc. 79 2002 203 210
6. T.R. Govindachari, M.V. Lakshmikantham, and S. Rajadurai Chem. Ind. 1960 664
7. T.R. Govindachari, M.V. Lakshmikantham, and S. Rajadurai Tetrahedron 14 1961 284 287
8. B. Chauncy, and E. Gellert Aust. J. Chem. 23 1970 2503 2516
9. R.B. Herbert, and C.J. Moody J. Chem. Soc. D 1970 121
10. A.J. Liepa, and R.E. Summons J. Chem. Soc., Chem. Commun. 1977 826 827
11. S.M. Weinreb, N.A. Khatri, and J. Shringarpure J. Am. Chem. Soc. 101 1979 5073 5074
12. V.K. Mangla, and D.S. Bhakuni Tetrahedron 36 1980 2489 2490
13. N.A. Khatri, J. Shringarpure, H.F. Schmittthenner, and S.M. Weinreb J. Am. Chem. Soc. 103 1981 6387 6393
14. J.E. Cragg, R.B. Herbert, F.B. Jackson, C.J. Moody, and I.T. Nicolson J. Chem. Soc., Perkin Trans. 1 1982 2477 2485
15. H. Iida, M. Tanaka, and C. Kibayashi J. Chem. Soc., Chem. Commun. 1983 271 272
16. D.L. Comins, and L.A. Morgan Tetrahedron Lett. 32 1991 5919 5922
17. W.H. Pearson, and R. Walavalkar Tetrahedron 50 1994 12293 12304
18. A. Mclver, D.D. Young, and A. Deiteres Chem. Commun. 2008 4750 4752
19. S. Yamashita, N. Kurono, H. Senboku, M. Tokuda, and K. Orito Eur. J. Org. Chem. 2009 1173 1180
20. M.J. Niphakis, and G.I. Georg Org. Lett. 13 2011 196 199
21. X. Xu, Y. Liu, and C.-M. Park Angew. Chem., Int. Ed. 51 2012 1 6
22. G. Lahm, A. Stoye, and T. Opatz J. Org. Chem. 77 2012 6620 6623
23. T.F. Buckley III, and H. Rapoport J. Org. Chem. 48 1983 4222 4232
24. J.E. Nordlander, and F.G. Njoroge J. Org. Chem. 52 1987 1627 1630
25. M. Ihara, Y. Takino, K. Fukumoto, and T. Kametani Heterocycles 28 1989 63 65
26. D.L. Comins, X.H. Chen, and L.A. Morgan J. Org. Chem. 62 1997 7435 7438
27. Z. Jin, S.P. Li, Q.M. Wang, and R.Q. Huang Chin. Chem. Lett. 15 2004 1164 1166
28. A. Fürstner, and J.W.J. Kennedy Chem. - Eur. J. 12 2006 7398 7410
29. W. Zeng, and S.R. Chemler J. Org. Chem. 73 2008 6045 6047
30. Z.W. Wang, Z. Li, K.L. Wang, and Q.M. Wang Eur. J. Org. Chem. 2010 292 299
31. A. Stoye, and T. Opatz Org. Lett. 12 2010 2140 2141
32. X.M. Yang, Q. Shi, K.F. Bastow, and K.H. Lee Org. Lett. 12 2010 1416 1419
33. D.N. Mai, and J.P. Wolfe J. Am. Chem. Soc. 132 2010 12157 12159
34. S.-F. Hsu, C.-W. Ko, and Y.-T. Wu Adv. Synth. Catal. 353 2011 1756 1762
35. T.-L. Ho Symmetry. A Basis for Synthesis Design 1995 Wiley-Interscience New York, NY
36. A. McKillop, A.G. Turrell, D.W. Young, and E.C. Taylor J. Am. Chem. Soc. 102 1980 6504 6512
37. K.-I. Kanno, Y.H. Liu, A. Lesato, K. Nakajima, and T. Takahashi Org. Lett. 7 2005 5453 5456
38. K.H. Weisgraber, and U. Weiss Can. J. Chem. 49 1971 2366 2369
39. P. Beak, S.T. Kerrick, S.D. Wu, and J.X. Chu J. Am. Chem. Soc. 116 1994 3231 3239
40. M. Shimizu, I. Nagao, Y. Tomioka, and T. Hiyama Angew. Chem., Int. Ed. 47 2008 8096 8099
41. S.H. Kim, and E.H. Han Tetrahedron Lett. 41 2000 6479 6482
42. J.S. Drage, R.A. Earl, and P.C. Vollhardt J. Heterocycl. Chem. 19 1982 701 702
43. J. Lacour, D. Monchaud, G. Bernardinelli, and F. Favarger Org. Lett. 3 2001 1407 1410
44. Y. Wang, and D.J. Burton Org. Lett. 8 2006 5295 5298
45. K.C.M. Kurtz, R.P. Hsung, and Y.S. Zhang Org. Lett. 8 2006 231 234