Pure Appl. Chem., 2012, Vol. 84, No. 6, pp. 1329-1339
http://dx.doi.org/10.1351/PAC-CON-11-07-05
Published online 2011-10-02
gem-Dibromocyclopropanes and enzymatically derived cis-1,2-dihydrocatechols as building blocks in alkaloid synthesis
References
- 1. M. G. Banwell, N. (Y.) Gao, B. D. Schwartz, L. V. White. Top. Curr. Chem. In press. (http://dx.doi.org/10.1007/128_2011_217)
- 2. For reviews on methods for generating gem-dihalocyclopropanes and/or their exploitation in chemical synthesis, see.
- 2a. M. Pure Appl. Chem. 43, 439 (1975). ( . http://dx.doi.org/10.1351/pac197543030439)
- 2b. M. G. Banwell, M. E. Reum. In Advances in Strain in Organic Chemistry, Vol. 1, B. Halton (Ed.), pp. 19–64, JAI Press, London (1991).
- 2c. L. Xu, U. H. Brinker. In Synthetic Organic Sonochemistry, J.-L. Luche (Ed.), pp. 344–345, Plenum Press, New York (1998).
- 2d. M. Chem. Rev. 103, 1099 (2003). ( . http://dx.doi.org/10.1021/cr0100087)
- 2e. M. G. Curr. Org. Chem. 9, 1589 (2005). ( , D. A. S. Beck, P. C. Stanislawski, M. O. Sydnes, R. M. Taylor. http://dx.doi.org/10.2174/138527205774370469)
- 2f. B. Synlett 1975 (2006). , J. Harvey.
- 3. For reviews on methods for generating compounds such as 2 by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see.
- 3a. T. Aldrichim. Acta 32, 35 (1999). , D. Gonzalez, D. T. Gibson.
- 3b. M. G. Pure Appl. Chem. 75, 223 (2003). ( , A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle. http://dx.doi.org/10.1351/pac200375020223)
- 3c. R. A. Org. React. 63, 117 (2004). .
- 3d. T. Synlett 685 (2009). ( , J. W. Reed. http://dx.doi.org/10.1055/s-0028-1087946)
- 3e. M. G. Pure Appl. Chem. 83, 411 (2011). ( , A. L. Lehmann, R. S. Menon, A. C. Willis. http://dx.doi.org/10.1351/PAC-CON-10-10-21)
- 4a. J. R. Nat. Prod. Rep. 15, 107 (1998). ( . http://dx.doi.org/10.1039/a815107y)
- 4b. Z. Nat. Prod. Rep. 28, 1126 (2011). ( . http://dx.doi.org/10.1039/c0np00073f)
- 5. C. Tetrahedron 62, 9043 (2006). ( , C. Guillou. http://dx.doi.org/10.1016/j.tet.2006.07.005)
- 6. S. Phytochemistry 24, 2141 (1985). ( , K. S. Saini, S. Razdan. http://dx.doi.org/10.1016/S0031-9422(00)83001-0)
- 7. J. Phytochemistry 68, 1068 (2007). ( , J. J. Nair, C. Codina, J. Bastida, S. Pandey, J. Gerasimoff, C. Griffin. http://dx.doi.org/10.1016/j.phytochem.2007.01.006)
- 8. L. E. Helv. Chim. Acta 68, 745 (1985). ( , S. Sugai. http://dx.doi.org/10.1002/hlca.19850680324)
- 9. B. Phytother. Res. 17, 1220 (2003). ( , I. Orhan, J. Satayavivad. http://dx.doi.org/10.1002/ptr.1346)
- 10. M. Chem. Commun. 1086 (2004). ( , H. Imase, N. Chida. http://dx.doi.org/10.1039/b402762k)
- 11. O. B. J. Nat. Prod. 67, 1119 (2004). ( , T. Morikawa, S. Ando, H. Matsuda, M. Yoshikawa. http://dx.doi.org/10.1021/np030529k)
- 12. See, for example.
- 12a. M. Tetrahedron 63, 6977 (2007). ( , K. Sugie, H. Imase, Y. B. Yusof, T. Oishi, N. Chida. http://dx.doi.org/10.1016/j.tet.2007.05.041)
- 12b. N. T. J. Org. Chem. 73, 6258 (2008). ( , J. Chang, E.-J. Jung, C.-G. Cho. http://dx.doi.org/10.1021/jo8008353)
- 12c. J.-D. Synlett 3040 (2009). , S.-H. Wang, F.-M. Zhang, Y.-Q. Tu, Y.-Q. Zhang.
- 12d. A. D. Org. Lett. 11, 3160 (2009). ( , M. G. Banwell. http://dx.doi.org/10.1021/ol901230w)
- 13. H. M. J. Org. Chem. 26, 1617 (1961). ( , W. C. Wildman. http://dx.doi.org/10.1021/jo01064a076)
- 14. J. J. Org. Chem. 27, 748 (1962). ( , S. Winstein. http://dx.doi.org/10.1021/jo01050a012)
- 15. M. G. Aust. J. Chem. 47, 2235 (1994). ( , C. J. Cowden. http://dx.doi.org/10.1071/CH9942235)
- 16. A. L. Aust. J. Chem. 63, 1665 (2010). ( , A. C. Willis, M. G. Banwell. http://dx.doi.org/10.1071/CH10359)
- 17a. B. M. Acc. Chem. Res. 23, 34 (1990). ( . http://dx.doi.org/10.1021/ar00170a004)
- 17b. A. Angew. Chem., Int. Ed. Engl. 35, 662 (1996). ( , M. Sawamura, R. Kuwano, Y. Ito. http://dx.doi.org/10.1002/anie.199606621)
- 18. T. Tetrahedron Lett. 36, 6373 (1995). ( , C.-K. Jow, M. Cheung. http://dx.doi.org/10.1016/0040-4039(95)01316-A)
- 19. T. R. Nat. Protoc. 2, 2451 (2007). ( , C. S. Jeffrey, F. Shao. http://dx.doi.org/10.1038/nprot.2007.354)
- 20. M. Bull. Chem. Soc. Jpn. 49, 3363 (1976). ( , H. Otsuki, K. Nagao. http://dx.doi.org/10.1246/bcsj.49.3363)
- 21. P. J. Phytochemistry 65, 2893 (2004). ( , J. M. Agbedahunsi, A. Adegbulugbe. http://dx.doi.org/10.1016/j.phytochem.2004.08.052)
- 22. H. Org. Biomol. Chem. 9, 2809 (2011). ( , C. Giró-Mañas, V. L. Paddock, C. G. Bochet, A. J. P. White, G. Bernardinelli, I. Mann, W. Oppolzer, A. C. Spivey. http://dx.doi.org/10.1039/c0ob00895h)
- 23. L. V. J. Org. Chem. 76, 6250 (2011). ( , B. D. Schwartz, M. G. Banwell, A. C. Willis. http://dx.doi.org/10.1021/jo201005d)
- 24. For relevant examples of other nitrogen-centered radical cyclization processes, see.
- 24a. M. G. Heterocycles 68, 71 (2006). ( , D. W. Lupton. http://dx.doi.org/10.3987/COM-05-10575)
- 24b. B. D. Org. Lett. 12, 5210 (2010). ( , M. T. Jones, M. G. Banwell, I. A. Cade. http://dx.doi.org/10.1021/ol102249q)
- 25. C. C. R. J. Chem. Soc., Chem. Commun. 117 (1995). ( , D. R. Boyd, H. Dalton, N. D. Sharma, I. Brannigan, N. A. Kerley, G. N. Sheldrake, S. C. Taylor. http://dx.doi.org/10.1039/c39950000117)
- 26. N. B. Molecules 15, 7083 (2010). ( , S. Berkov, A. Elamrani, M. Benaissa, F. Viladomat, C. Codina, J. Bastida. http://dx.doi.org/10.3390/molecules15107083)
- 27. B. D. Tetrahedron Lett. 52, 4526 (2011). ( , M. G. Banwell, I. A. Cade. http://dx.doi.org/10.1016/j.tetlet.2011.06.050)
- 28. T. J. Am. Chem. Soc. 112, 9439 (1990). ( , J. D. Price, F. Rulin, T. Tsunoda. http://dx.doi.org/10.1021/ja00181a081)