Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH13287
RESEARCH FRONT
Contents Vol 66(8)

Studies on the Enantioselective Synthesis of Carbazolones as Intermediates in Aspidosperma and Kopsia Alkaloid Synthesis*

Christopher J. Gartshore A and David W. Lupton A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B Corresponding author. Email: david.lupton@monash.edu

Australian Journal of Chemistry 66(8) 882-890 https://doi.org/10.1071/CH13287
Submitted: 3 June 2013  Accepted: 5 July 2013   Published: 12 August 2013

Abstract

Two strategies for the assembly of homochiral carbazolones have been investigated. The first exploited desymmetrisation of 1,3-cyclohexadione derivatives however this failed to deliver satisfactory outcomes. An orthogonal route exploiting palladium catalysed decarboxylative allylation of racemic carbazolone β-ketoesters has been developed. Herein we report full details on the development of this reaction and clarify apparent discrepancies between our preliminary reports and those of Shao.


References

[1]  (a) For Aspidosperma and Kopsia alkaloids see: J. M. Lopchuk, Heterocyc. Chem. 2011, 23, 1.
         | 1:CAS:528:DC%2BC38XhsFCgs7o%3D&md5=75c2d188f80aafc3414868a2aabd3b43CAS |
      (b) J. E. Saxton, Alkaloids 1998, 50, 415.
      (c) T.-S. Kam, K.-H. Lim, Alkaloids 2008, 66, 1.

[2]  (a) For reviews on carbazole natural products: A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XltFGitLw%3D&md5=5d504eba6186882c995cfef2cc25f997CAS | 22480243PubMed |
      (b) T. Janosik, N. Wahlström, J. Bergman, Tetrahedron 2008, 64, 9159.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) J. d’Angelo, D. Desmaële, Tetrahedron Lett. 1990, 31, 879.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXltlamt7g%3D&md5=10b276a8df5c3d0522daeb571ab5b00cCAS |
      (b) D. Desmaële, J. d’Angelo, J. Org. Chem. 1994, 59, 2292.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  C. J. Gartshore, D. W. Lupton, Angew. Chem. Int. Ed. 2013, 52, 4113.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVGlsL4%3D&md5=340bdd22023d0905e3c2b8f9cd6952cbCAS |

[5]  D. B. Ramachary, M. Kishor, J. Org. Chem. 2007, 72, 5056.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtFCnsLk%3D&md5=8c5f483de62051339f946990a6612f23CAS | 17552564PubMed |

[6]  B. Butler, T. Schultz, N. S. Simpkins, Chem. Commun. 2006, 3634.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xotl2qtb8%3D&md5=c58c01833c75c7a4df992df8d19f4d19CAS |

[7]  P. Renouf, J.-M. Poirier, P. Duhamel, J. Chem. Soc., Perkin Trans. 1 1997, 1739.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXktlarsrY%3D&md5=b186fa5158fa1f07d68a175ce3de7f3dCAS |

[8]  T. D. Poisson, C. Papamiceal, G. Dupas, F. Marsais, V. Levacher, Synlett 2007, 381.
         | 1:CAS:528:DC%2BD2sXis1Wht7k%3D&md5=e87e6b603d3b9d59a7c446be1f1f429eCAS |

[9]  (a) For reviews on decarboxylative allylation see: J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmtVehtQ%3D%3D&md5=4d346da60af46d5f52cbbb3d27e1f9deCAS | 21235271PubMed |
      (b) J. T. Mohr, B. M. Stoltz, Chem. Asian J. 2007, 2, 1476.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXks1Shsr8%3D&md5=9e6c65c69032c44c002d086aa7c76e88CAS |

[11]  B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. Int. Ed. 2006, 45, 3109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkvFKnsbo%3D&md5=9fc8eecae1adbffcd34df8ffa41ef7e3CAS |

[12]  For a detailed examination of the 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.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtlejtrY%3D&md5=8588b029ae933fb7383194b2554a5208CAS | 23447555PubMed |

[13]  D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. Whute, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2011, 4, 130.
         | Crossref | GoogleScholarGoogle Scholar | 22270628PubMed |

[14]  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.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjvVelsrs%3D&md5=04eb73247a2494e83e01079150fee428CAS |

[15]  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.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvFyrtbw%3D&md5=6805cc3eb230a33560d305042737176aCAS | 16647264PubMed |

[16]  For use of the Tosyl see: D. D. Evans, Aust. J. Chem. 1973, 26, 2555.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXlsVKgsL0%3D&md5=b0471faf0b586819beeb4ddbb557bcc1CAS |

[17]  For the use of this reagent and literature associated with allyl chloroformate see: B. M. Trost, J. Xu, J. Org. Chem. 2007, 72, 9372.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1arsb3I&md5=edff624e39c8e2af1024bcbb4e9aab8eCAS | 17963405PubMed |

[18]  (a) L. N. Mander, S. P. Sethi, Tetrahedron Lett. 1983, 24, 5425.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXhsFGrtL0%3D&md5=31d913824bd807f0676c35f6396b2f07CAS |
      (b) D. M. X. Donnelly, J.-P. Finet, B. A. Rattigan, J. Chem. Soc., Perkin Trans. 1 1993, 1729.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  For decarboxylative allylation of racemic β-keto esters: J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed. 2005, 44, 6924.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1alsr%2FO&md5=ac2875046298501fd6c01cb72a5c92d0CAS |

[20]  P. Jing, Z. Yang, C. Zhao, H. Zheng, B. Fang, X. Xie, X. She, Chemistry 2012, 18, 6729.
         | 1:CAS:528:DC%2BC38XmtlWgtr8%3D&md5=26d1a7512b55187df62bf82edbb4a359CAS | 22549799PubMed |

[21]  K. Asahi, H. Nishino, Tetrahedron 2008, 64, 1620.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXotlansg%3D%3D&md5=4e5d2b1ce7042d59bda1fcd9d1813bc4CAS |

[22]  J. Cuomo, R. A. Olofson, J. Org. Chem. 1979, 44, 1016.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXhtlKrsLc%3D&md5=41093a5692e0763eb9da2a6e2df027b4CAS |