Studies on the enantioselective synthesis of carbazolones as intermediates in aspidosperma and kopsia alkaloid synthesis

Australian Journal of Chemistry

Volumn 66, Issue 8, 2013, Pages 882-890

  Gartshore, Christopher J ^a   Lupton, David W ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-CYCLOHEXADIONE; ALKALOID SYNTHESIS; ASPIDOSPERMA; ENANTIOSELECTIVE SYNTHESIS; HOMOCHIRAL; KETO ESTER;

CHEMISTRY;

SYNTHESIS (CHEMICAL);

EID: 84882575093     PISSN: 00049425     EISSN: 14450038     Source Type: Journal    
DOI: 10.1071/CH13287     Document Type: Article

References (28)

1. J. M. Lopchuk, Prog. 2011, Heterocyc. Chem. 2011, 23, 1.
2. J. E. Saxton, Alkaloids 1998, 50, 415.
3. T.-S. Kam, K.-H. Lim, Alkaloids 2008, 66, 1.
4. For reviews on carbazole natural products: (a) A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193. doi:10.1021/CR200447S
5. T. Janosik, N. Wahlström, J. Bergman, Tetrahedron 2008, 64, 9159. doi:10.1016/J.TET.2008.06.101
6. J. d'Angelo, D. Desmaële, Tetrahedron Lett. 1990, 31, 879. doi:10.1016/S0040-4039(00)94653-7
7. D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292. doi:10.1021/JO00088A008
8. C. J. Gartshore, D. W. Lupton, Angew. Chem. Int. Ed. 2013, 52, 4113. doi:10.1002/ANIE.201209069
9. D. B. Ramachary, M. Kishor, J. Org. Chem. 2007, 72, 5056. doi:10.1021/JO070277I
10. B. Butler, T. Schultz, N. S. Simpkins, Chem. Commun. 2006, 3634. doi:10.1039/B606864B
11. P. Renouf, J.-M. Poirier, P. Duhamel, J. Chem. Soc., Perkin Trans. 1 1997, 1739. doi:10.1039/A606001C
12. T. D. Poisson, C. Papamiceal, G. Dupas, F. Marsais, V. Levacher, Synlett 2007, 381.
13. For reviews on decarboxylative allylation see: J. D. Weaver, A. Recio III, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846. doi:10.1021/CR1002744
14. J. T. Mohr B. M. Stoltz Chem. Asian J 2007 2 1476 doi:10.1002/ASIA. 200700183
15. A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745. doi:10.1002/EJOC.201201761
16. B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. Int. Ed. 2006, 45, 3109. doi:10.1002/ANIE.200504421
17. For a detailed examination of he effect of electronic and steric parameters on allylations with N-heterocycles see: N. B. Bennett, D. C. Duquette, J. Kim, W.-B. Liu, A. N. Marziale, D. C. Behenna, S. C. Virgil, B. M. Stoltz, Chem.-Eur. J. 2013, 19, 4414. doi:10.1002/CHEM.201300030
18. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. Whute, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2011, 4, 130. doi:10.1038/NCHEM.1222
19. Z. Li, S. Zhang, S. Wu, X. Shen, L. Zou, F. Wang, X. Li, F. Peng, H. Zhang, Z. Shao, Angew. Chem. Int. Ed. 2013, 52, 4117. doi:10.1002/ANIE.201209878
20. For example: G. Romeo, L. Materia, V. Pittala, M. Modica, L. Salerno, M. Siracusa, F. Russo, K. P. Minneman, Bioorg. Med. Chem. 2006, 14, 5211. doi:10.1016/J.BMC.2006.04.002
21. For use of the Tosyl see: D. D. Evans, Aust. J. Chem. 1973, 26, 2555. doi:10.1071/CH9732555
22. For the use of this reagent and literature associated with allyl chloroformate see: B. M. Trost, J. Xu, J. Org. Chem. 2007, 72, 9372. doi:10.1021/JO7016313
23. L. N. Mander, S. P. Sethi, Tetrahedron Lett. 1983, 24, 5425. doi:10.1016/S0040-4039(00)87886-7
24. D. M. X. Donnelly J.-P. Finet B. A. Rattigan J. Chem. Soc.Perkin Trans 1 1993 1729 doi:10.1039/P19930001729
25. For decarboxylative allylation of racemic b-keto esters: J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed. 2005, 44, 6924. doi:10.1002/ANIE.200502018
26. P. Jing, Z. Yang, C. Zhao, H. Zheng, B. Fang, X. Xie, X. She, Chemistry 2012, 18, 6729.
27. K. Asahi, H. Nishino, Tetrahedron 2008, 64, 1620. doi:10.1016/J.TET. 2007.12.017
28. J. Cuomo, R. A. Olofson, J. Org. Chem. 1979, 44, 1016. doi:10.1021/JO01320A034