Pure and Applied Chemistry

Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 411-423

http://dx.doi.org/10.1351/PAC-CON-10-10-21

Published online 2011-02-01

New methods for the synthesis of certain alkaloids and terpenoids

References

• 1a. I. Paterson, E. A. Anderson. Science 310, 451 (2005). (http://dx.doi.org/10.1126/science.1116364)
• 1b. K. C. Nicolaou, S. A. Snyder. Angew. Chem., Int. Ed. 44, 1012 (2005). (http://dx.doi.org/10.1002/anie.200460864)
• 1c. R. M. Wilson, S. J. Danishefsky. J. Org. Chem. 71, 8329 (2006). (http://dx.doi.org/10.1021/jo0610053)
• 1d. M. G. Banwell. Tetrahedron 64, 4669 (2008). (http://dx.doi.org/10.1016/j.tet.2008.03.051)
• 2a. M. Makosza. Pure. Appl. Chem. 43, 439 (1975). (http://dx.doi.org/10.1351/pac197543030439)
• 2b. L. Xu, U. H. Brinker. In Synthetic Organic Sonochemistry, J.-L. Luche (Ed.), pp. 344–345, Plenum Press, New York (1998).
• 3a. M. G. Banwell, M. E. Reum. In Advances in Strain in Organic Chemistry, B. Halton (Ed.), Vol. 1, pp. 19–64, JAI Press, London (1991).
• 3b. M. Fedoryński. Chem. Rev. 103, 1099 (2003). (http://dx.doi.org/10.1021/cr0100087)
• 3c. M. G. Banwell, D. A. S. Beck, P. C. Stanislawski, M. O. Sydnes, R. M. Taylor. Curr. Org. Chem. 9, 1589 (2005). (http://dx.doi.org/10.2174/138527205774370469)
• 3d. B. Halton, J. Harvey. Synlett 1975 (2006).
• 4. P. C. Stanislawski, A. C. Willis, M. G. Banwell. Chem. Asian J. 2, 1127 (2007). (http://dx.doi.org/10.1002/asia.200700155)
• 5. See: S. W. Baldwin, J. S. Debenham. Org. Lett. 2, 99 (2000) and refs. cited therein. (http://dx.doi.org/10.1021/ol9911472)
• 6a. C. Bru, C. Guillou. Tetrahedron 62, 9043 (2006). (http://dx.doi.org/10.1016/j.tet.2006.07.005)
• 6b. A. Padwa, M. A. Brodney, M. Dimitroff, B. Liu, T. Wu. J. Org. Chem. 66, 3119 (2001) and refs. cited therein. (http://dx.doi.org/10.1021/jo010020z)
• 7. A. L. Lehmann, A. C. Willis, M. G. Banwell. Aust. J. Chem. 63, 1665 (2010). (http://dx.doi.org/10.1071/CH10359)
• 8a. A. S. K. Hashmi, G. J. Hutchings. Angew. Chem., Int. Ed. 45, 7896 (2006). (http://dx.doi.org/10.1002/anie.200602454)
• 8b. A. Fürstner, P. W. Davies. Angew. Chem., Int. Ed. 46, 3410 (2007). (http://dx.doi.org/10.1002/anie.200604335)
• 8c. D. J. Gorin, F. D. Toste. Nature 446, 395 (2007). (http://dx.doi.org/10.1038/nature05592)
• 8d. A. S. K. Hashmi. Nature 449, 292 (2007). (http://dx.doi.org/10.1038/449292a)
• 8e. A. S. K. Hashmi. Chem. Rev. 107, 3180 (2007). (http://dx.doi.org/10.1021/cr000436x)
• 8f. Z. Li, C. Brouwer, C. He. Chem. Rev. 108, 3239 (2008). (http://dx.doi.org/10.1021/cr068434l)
• 8g. A. Arcadi. Chem. Rev. 108, 3266 (2008). (http://dx.doi.org/10.1021/cr068435d)
• 8h. E. Jiménez-Núñez, A. M. Echavarren. Chem. Rev. 108, 3326 (2008). (http://dx.doi.org/10.1021/cr0684319)
• 8i. D. J. Gorin, B. D. Sherry, F. D. Toste. Chem. Rev. 108, 3351 (2008). (http://dx.doi.org/10.1021/cr068430g)
• 9. R. S. Menon, A. D. Findlay, A. C. Bissember, M. G. Banwell. J. Org. Chem. 74, 8901 (2009). (http://dx.doi.org/10.1021/jo902032p)
• 10. R. S. Menon, M. G. Banwell. Org. Biomol. Chem. 8, 5483 (2010). (http://dx.doi.org/10.1039/c0ob00487a)
• 11. C. Menut, P. Cabalion, E. Hnawia, H. Agnaniet, J. Waikedre, A. Fruchier. Flavour Fragrance J. 20, 621 (2005). (http://dx.doi.org/10.1002/ffj.1509)
• 12. K. A. Porter, A. Schier, H. Schmidbaur. Organometallics 22, 4922 (2003). (http://dx.doi.org/10.1021/om030575f)
• 13. G. J. Zylstra, D. T. Gibson. J. Biol. Chem. 264, 14940 (1989).
• 14. For reviews on methods for generating compounds such as 41 by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see.
• 14a. T. Hudlicky, D. Gonzalez, D. T. Gibson. Aldrichim. Acta 32, 35 (1999).
• 14b. M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle. Pure Appl. Chem. 75, 223 (2003). (http://dx.doi.org/10.1351/pac200375020223)
• 14c. R. A. Johnson. Org. React. 63, 117 (2004).
• 14d. T. Hudlicky, J. W. Reed. Synlett 685 (2009). (http://dx.doi.org/10.1055/s-0028-1087946)
• 15a. Vitamin C: M. G. Banwell, S. Blakey, G. Harfoot, R. W. Longmore. Aust. J. Chem. 52, 137 (1999). (http://dx.doi.org/10.1071/C98157)
• 15b. (–)-Cladospolide A: M. G. Banwell, D. T. J. Loong. Org. Biomol. Chem. 2, 2050 (2004). (http://dx.doi.org/10.1039/b401829j)
• 15c. (+)-Brunsvigine: M. G. Banwell, O. J. Kokas, A. C. Willis. Org. Lett. 9, 3503 (2007). (http://dx.doi.org/10.1021/ol071344y)
• 15d. Phellodonic acid: T. A. Reekie, K. A. B. Austin, M. G. Banwell, A. C. Willis. Aust. J. Chem. 61, 94 (2008). (http://dx.doi.org/10.1071/CH07403)
• 15e. Platencin: K. A. B. Austin, M. G. Banwell, A. C. Willis. Org. Lett. 10, 4465 (2008). (http://dx.doi.org/10.1021/ol801647h)
• 15f. ent-Narciclasine: M. Matveenko, M. G. Banwell, A. C. Willis. Tetrahedron 64, 4817 (2008). (http://dx.doi.org/10.1016/j.tet.2008.01.113)
• 15g. Tamiflu™: M. Matveenko, A. C. Willis, M. G. Banwell. Tetrahedron Lett. 49, 7018 (2008). (http://dx.doi.org/10.1016/j.tetlet.2008.09.130)
• 15h. Panepophenanthrin: D. M. Pinkerton, M. G. Banwell, A. C. Willis. Org. Lett. 11, 4290 (2009). (http://dx.doi.org/10.1021/ol9016657)
• 15i. (–)-Tricholomenyn A: D. M. Pinkerton, M. G. Banwell, A. C. Willis. Aust. J. Chem. 62, 1639 (2009). (http://dx.doi.org/10.1071/CH09469)
• 15j. Lycorine degradation product: M. T. Jones, B. D. Schwartz, A. C. Willis, M. G. Banwell. Org. Lett. 11, 3506 (2009). (http://dx.doi.org/10.1021/ol901364n)
• 15k. L-783,290: A. Lin, A. C. Willis, M. G. Banwell. Tetrahedron Lett. 51, 1044 (2010). (http://dx.doi.org/10.1016/j.tetlet.2009.12.067)
• 15l. (+)-Conatussin B: D. J.-Y. D. Bon, M. G. Banwell, A. C. Willis. Tetrahedron 66, 7807 (2010). (http://dx.doi.org/10.1016/j.tet.2010.07.059)
• 15m. (+)-Galanthamine: M. G. Banwell, X. Ma, O. P. Karunaratne, A. C. Willis. Aust. J. Chem. 63, 1437 (2010). (http://dx.doi.org/10.1071/CH10201)
• 16a. D. R. Boyd, N. D. Sharma, S. A. Barr, H. Dalton, J. Chima, G. Whited, R. Seemayer. J. Am. Chem. Soc. 116, 1147 (1994). (http://dx.doi.org/10.1021/ja00082a053)
• 16b. C. C. R. Allen, D. R. Boyd, H. Dalton, N. D. Sharma, I. Brannigan, N. A. Kerley, G. N. Sheldrake, S. C. Taylor. J. Chem. Soc., Chem. Commun. 117 (1995). (http://dx.doi.org/10.1039/c39950000117)
• 17. J. Wang, S. Kodali, S. H. Lee, A. Galgoci, R. Painter, K. Dorso, F. Racine, M. Motyl, L. Hernandez, E. Tinney, S. L. Colletti, K. Herath, R. Cummings, O. Salazar, I. González, A. Basilio, F. Vicente, O. Genilloud, F. Pelaez, H. Jayasuriya, K. Young, D. F. Cully, S. B. Singh. Proc. Natl. Acad. Sci. USA 104, 7612 (2007). (http://dx.doi.org/10.1073/pnas.0700746104)
• 18a. K. C. Nicolaou, G. S. Tria, D. Edmonds. Angew. Chem., Int. Ed. 47, 1780 (2008). (http://dx.doi.org/10.1002/anie.200800066)
• 18b. J. Hayashida, V. H. Rawal. Angew. Chem., Int. Ed. 47, 4373 (2008). (http://dx.doi.org/10.1002/anie.200800756)
• 19. See, for example: M. G. Banwell, C. Chun, A. J. Edwards, M. M. Vögtle. Aust. J. Chem. 56, 861 (2003). (http://dx.doi.org/10.1071/CH03112)