Aza-Quaternary Scaffolds from Selective Bond Cleavage of Bridgehead-Substituted 7-Azabicyclo[2.2.1]heptane: Total Synthesis of (+)-Cylindricines C-E and (-)-Lepadiformine A

Chemistry - A European Journal

Volumn 21, Issue 37, 2015, Pages 13120-13126

  Pandey, Ganesh ^a   Janakiram, Vaitla ^a  

^a SANJAY GANDHI POSTGRADUATE INSTITUTE OF MEDICAL SCIENCES   (India)

Author keywords

alkaloids; asymmetric synthesis; rearrangement; spiro compounds; total synthesis

Indexed keywords

ALKALOIDS; METABOLITES; SCAFFOLDS;

ASYMMETRIC SYNTHESIS; BOND CLEAVAGES; BOND FRAGMENTATION; DESYM-METRIZATION; MARINE ALKALOIDS; REARRANGEMENT; SPIRO COMPOUNDS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

7-AZABICYCLO(2.2.1)HEPTANE; ALKALOID; CYLINDRICINE D; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; LEPADIFORMINE; QUINOLONE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AZA COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; HETEROCYCLIC COMPOUNDS, 3-RING; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; MOLECULAR STRUCTURE; QUINOLONES; STEREOISOMERISM;

EID: 84940460184     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501859     Document Type: Article

References (62)

1. D. L. J. Clive, M. Yu, J. Wang, V. S. C. Yeh, S. Kang, Chem. Rev. 2005, 105, 4483
2. S. A. A. El Bialy, H. Braun, L. F. Tietze, Synthesis 2004, 2249.
3. H. M. Kantarjian, M. Talpaz, V. Santini, A. Murgo, B. Cheson, S. M. O'Brien, Cancer 2001, 92, 1591
4. G. Alvaro, E. Castiglioni, A. Marasco, Patent PCT/WO 2009133135A1 20091105, Glaxo Wellcome Manufacturing Pte Ltd, Singapore.
5. G. Dake, Tetrahedron, 2006, 62, 3467.
6. I. Marek, A. Masarwa, P.-O. Delaye, M. Leibeling, Angew. Chem. Int. Ed. 2015, 54, 414
7. Angew. Chem. 2015, 127, 424.
8. A. P. Kozikowski, M. P. Kuniak, J. Org. Chem. 1978, 43, 2083
9. G. Pandey, K. N. Tiwari, V. G. Puranik, Org. Lett. 2008, 10, 3611.
10. E. Moreno-Clavijo, A. J. Moreno-Vargas, R. Kieffer, T. Sigstam, A. T. Carmona, I. Robina, Org. Lett. 2011, 13, 6244
11. G. Pandey, R. Varkhedkar, D. Tiwari, Org. Biomol. Chem. 2015, 13, 4438.
12. A. Hernandez, M. Marcos, H. Rapoport, J. Org. Chem. 1995, 60, 2683
13. W. F. J. Karstens, M. J. Moolenaar, F. P. J. T. Rutjes, U. Grabowska, W. N. Speckamp, H. Hiemstra, Tetrahedron Lett. 1999, 40, 8629
14. D. L. J. Clive, V. S. C. Yeh, Tetrahedron Lett. 1998, 39, 4789
15. E. Albertini, A. Barco, S. Benetti, C. D. Risi, G. P. Pollini, V. Zanirato, Tertrahedron 1997, 53, 17177
16. M. Node, K. Nishide, T. Fujiwara, S. Ichihashi, Chem. Commun. 1998, 2363.
17. M. Wang, M. Feng, B. Tang, X. Jiang, Tetrahedron Lett. 2014, 55, 7147.
18. G. Pandey, S. Rajender, Chem. Eur. J. 2011, 17, 6304
19. G. Pandey, S. K. Tiwari, R. S. Singh, R. S. Mali, Tetrahedron Lett. 2001, 42, 3947.
20. I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105
21. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873
22. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969
23. M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853.
24. R. Li, D. S. Larsen, S. Brooker, New J. Chem. 2003, 27, 1353.
25. T. B. Poulsen, L. Bernardi, J. Aleman, J. Overgaard, K. A. Jorgensen, J. Am. Chem. Soc. 2007, 129, 441.
26. T. Ikariya, S. Hashiguchi, K. Murata, R. Noyori, Org. Synth. 2005, 82, 10.
27. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134
28. Angew. Chem. 2006, 118, 7292
29. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993
30. E. A. Anderson, Org. Biomol. Chem. 2011, 9, 3997.
31. A. J. Blackman, C. Li, D. C. R. Hockless, B. W. Skelton, A. H. White, Tetrahedron 1993, 49, 8645
32. C. Li, A. J. Blackman, Aust. J. Chem. 1995, 48, 955
33. C. Li, A. J. Blackman, Aust. J. Chem. 1994, 47, 1355.
34. J. F. Biard, S. Guyot, C. Roussakis, J. F. Verbist, J. Vercauteren, F. Weber, K. Boukef, Tetrahedron Lett. 1994, 35, 2691
35. M. Jugé, N. Grimaud, J. F. Biard, M. P. Sauviat, M. Nabil, J. F. Verbist, J. Y. Petit, Toxicon 2001, 39, 1231.
36. S. M. Weinreb, Acc. Chem. Res. 2003, 36, 59
37. C. Kibayashi, S. Aoyagi, H. Abe, Bull. Chem. Soc. Jpn. 2003, 76, 2059
38. P. Schär, S. Cren, P. Renaud, Chimia 2006, 60, 131
39. S. M. Weinreb, Chem. Rev. 2006, 106, 2531
40. J. Liu, R. P. Hsung, Chemtracts: Org. Chem. 2005, 18, 321.
41. G. A. Molander, M. J. Roenn, J. Org. Chem. 1999, 64, 5183
42. B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 4599.
43. J. J. Swidorski, J. Wang, R. P. Hsung, Org. Lett. 2006, 8, 777.
44. H. Abe, S. Aoyagi, C. Kibayashi, J. Am. Chem. Soc. 2005, 127, 1473
45. J. Liu, R. P. Hsung, S. D. Peters, Org. Lett. 2004, 6, 3989
46. P. Sun, C. Sun, S. M. Weinreb, J. Org. Chem. 2002, 67, 4337.
47. S. Canesi, D. Bouchu, M. A. Ciufolini, Angew. Chem. Int. Ed. 2004, 43, 4336
48. Angew. Chem. 2004, 116, 4436.
49. T. Shibuguchi, H. Mihara, A. Kuramochi, S. Sakuraba, T. Ohshima, M. Shibasaki, Angew. Chem. Int. Ed. 2006, 45, 4635
50. Angew. Chem. 2006, 118, 4751.
51. X. Xiao, D. Bai, Synlett 2001, 0535.
52. H. Kinoshita, H. Shinokubo, K. Oshima, Angew. Chem. Int. Ed. 2005, 44, 2397
53. Angew. Chem. 2005, 117, 2449.
54. B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. Int. Ed. Engl. 1997, 36, 2632
55. Angew. Chem. 1997, 109, 2746.
56. P. G. Gasman, S. J. Burns, K. B. Pfister, J. Org. Chem. 1993, 58, 1449.
57. P. Schär, P. Renaud, Org. Lett. 2006, 8, 1569
58. J. J. Caldwell, D. Craig, Angew. Chem. Int. Ed. 2007, 46, 2631
59. Angew. Chem. 2007, 119, 2685.
60. J. Liu, J. J. Swidorski, S. D. Peters, R. P. Hsung, J. Org. Chem. 2005, 70, 3898.
61. H. Abe, S. Aoyagi, C. Kibayashi, Angew. Chem. Int. Ed. 2002, 41, 3017
62. Angew. Chem. 2002, 114, 3143.