Skip to content
Publicly Available Published by De Gruyter December 13, 2012

The boronic acid Mannich reaction in alkaloid synthesis

  • Stephen G. Pyne , Andrew S. Davis , Thunwadee Ritthiwigrom , Christopher W. G. Au , Kongdech Savaspun and Matthew Wotherspoon

Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.


Conference

International Conference on Organic Synthesis (ICOS-19), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 19th, Melbourne, Australia, 2012-07-01–2012-07-06


References

1 10.1016/S0031-9422(00)00451-9, A. A. Watson, G. W. J. Fleet, N. Asano, R. J. Molyneux, R. J. Nash. Phytochemistry56, 265 (2001).Search in Google Scholar

2 N. Asano. Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Wiley-VCH, Weinheim (2008).Search in Google Scholar

3 10.1016/S0040-4039(00)61625-8, N. A. Petasis, I. Akritopoulou. Tetrahedron Lett.34, 583 (1993).Search in Google Scholar

4 R. A. Batey. In Boronic Acids, D. G. Hall (Ed.), pp. 281–299, Wiley-VCH, Weinheim (2005).Search in Google Scholar

5 10.1021/cr100108k, N. R. Candeias, F. Montalbano, P. M. S. D. Cal, P. M. P. Gois. Chem. Rev.110, 6169 (2010).Search in Google Scholar

6 T. Matsumura, M. Kasai, T. Hayashi, M. Arisawa, Y. Momose, I. Arai, S. Amagaya, Y. Komatsu. Pharm. Biol.38, 302 (2000).Search in Google Scholar

7 10.1021/jo049806y, A. S. Davis, S. G. Pyne, B. W. Skelton, A. H. White. J. Org. Chem.69, 3139 (2004).Search in Google Scholar

8 10.1021/jo060823s, N. S. Karanjule, S. D. Markad, D. D. Dhavale. J. Org. Chem.71, 6273 (2006).Search in Google Scholar

9 10.1016/j.tet.2005.07.014, Z. Zhao, L. Song, P. S. Mariano. Tetrahedron61, 8888 (2005).Search in Google Scholar

10 10.1016/0040-4039(96)01956-9, A. W. Bell, L. Pickering, A. A. Watson, R. J. Nash, R. C. Griffiths, M. G. Jones, G. W. J. Fleet. Tetrahedron Lett.37, 8561 (1996).Search in Google Scholar

11 10.1016/j.tet.2008.02.110, A. D. Davis, T. Ritthiwigrom, S. G. Pyne. Tetrahedron64, 4868 (2008).Search in Google Scholar

12 10.1021/ol8009144, T. Ritthiwigrom, S. G. Pyne. Org. Lett.10, 2769 (2008).Search in Google Scholar PubMed

13 10.1021/jo902355p, T. Ritthiwigrom, A. C. Willis, S. G. Pyne. J. Org. Chem.75, 815 (2010).Search in Google Scholar PubMed

14 10.1021/np900435d, C. Parmeggiani, D. Martella, F. Cardona, A. Goti. J. Nat. Prod.72, 2058 (2009).Search in Google Scholar

15 R. J. Nash, P. I. Thomas, R. D. Waigh, G. W. J. Fleet, M. R. Wormald, P. M. de Q. Lilley, D. J. Watkin. Tetrahedron Lett.35, 7849 (1994).Search in Google Scholar

16 10.1016/j.tetasy.2006.10.005, J. Van Ameijde, G. Horne, M. R. Wormald, R. A. Dwek, R. J. Nash, P. W. Jones, E. L. Evinson, G. W. J. Fleet. Tetrahedron: Asymmetry17, 2702 (2006).Search in Google Scholar

17 M. R. Wormald, R. J. Nash, A. A. Watson, B. K. Bhadoria, R. Langford, M. Sims, G. W. J. Fleet. Carbohydr. Lett.2, 169 (1996).Search in Google Scholar

18 10.1016/S0008-6215(99)00043-9, A. Kato, I. Adachi, M. Miyauchi, K. Ikeda, T. Komae, H. Kizu, Y. Kameda, A. A. Watson, R. J. Nash, M. R. Wormald, G. W. J. Fleet, N. Asano. Carbohydr. Res.316, 95 (1999).Search in Google Scholar

19 10.1016/S0957-4166(99)00508-X, N. Asano, H. Kuroi, K. Ikeda, H. Kizu, Y. Kameda, A. Kato, I. Adachi, A. A. Watson, R. J. Nash, G. W. J. Fleet. Tetrahedron: Asymmetry11, 1 (2000).Search in Google Scholar

20 10.1021/np020296h, T. Yamashita, K. Yasuda, H. Kizu, Y. Kameda, A. A. Watson, R. J. Nash, G. W. J. Fleet, N. Asano. J. Nat. Prod.65, 1875 (2002).Search in Google Scholar PubMed

21 10.1021/np0499721, N. Asano, K. Ikeda, M. Kasahara, Y. Arai, H. Kizu. J. Nat. Prod.67, 846 (2004).Search in Google Scholar PubMed

22 10.1021/np0700826, A. Kato, N. Kato, I. Adachi, J. Hollinshead, G. W. J. Fleet, C. Kuriyama, K. Ikeda, N. Asano, R. J. Nash. J. Nat. Prod.70, 993 (2007).Search in Google Scholar PubMed

23 10.1039/b918233k, C. W. G. Au, R. J. Nash, S. G. Pyne. Chem. Commun.46, 713 (2010).Search in Google Scholar PubMed

24 10.1016/j.tet.2003.08.003, P. Evans, M. Leffray. Tetrahedron59, 7973 (2003).Search in Google Scholar

25 10.1021/jo0610661, C. W. G. Au, S. G. Pyne. J. Org. Chem.71, 7097 (2006).Search in Google Scholar PubMed

26 K. Savaspun, S. G. Pyne. Unpublished results.Search in Google Scholar

27 10.1016/j.tetlet.2009.06.072, T. Sengoku, Y. Satoh, M. Takahashi, H. Yoda. Tetrahedron Lett.50, 4937 (2009).Search in Google Scholar

28 10.1021/ol201749c, W. Zhang, K. Sato, A. Kato, Y.-M. Jia, X.-G. Hu, F. X. Wilson, F. X. R. van Well, G. Horne, G. W. J. Fleet, R. J. Nash, C.-Y. Yu. Org. Lett.13, 4414 (2011).Search in Google Scholar PubMed

Online erschienen: 2012-12-13
Erschienen im Druck: 2012-12-13

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 16.4.2024 from https://www.degruyter.com/document/doi/10.1351/PAC-CON-12-07-05/html
Scroll to top button