Pure and Applied Chemistry

Pure Appl. Chem., 2013, Vol. 85, No. 6, pp. 1203-1213

http://dx.doi.org/10.1351/PAC-CON-12-09-15

Published online 2013-03-27

Synthesis of complex oxygenated heterocycles

References

• 1a. M. D'Ambrosio, A. Guerriero, C. Debitus, F. Pietra. Helv. Chim. Acta 79, 51 (1996); (http://dx.doi.org/10.1002/hlca.19960790107)
• 1b. for recent works concerning leucascandrolide A, see: L. Ferrié, S. Reymond, P. Capdevielle, J. Cossy. Org. Lett. 9, 2461 (2007). (http://dx.doi.org/10.1021/ol070670a)
• 1c. L. Ferrié, L. Boulard, F. Pradaux, S. BouzBouz, S. Reymond, P. Capdevielle, J. Cossy. J. Org. Chem. 73, 1864, (2008). (http://dx.doi.org/10.1021/jo701315h)
• 1d. K. Lee, H. Kim, J. Hong. Org. Lett. 13, 2722 (2011). (http://dx.doi.org/10.1021/ol200824r)
• 2. W. Meng, B. A. Ellsworth, A. A. Nirrscht, P. J. McCann, M. Patel, R. N. Girotra, G. Wu, P. M. Sher, E. P. Morrison, S. A. Biller, R. Zahler, P. P. Deshplande, A. Pullockaran, D. L. Hagan, N. Morgan, J. R. Taylor, M. T. Obermeier, W. G. Humphreys, A. Khanna, L. Discenza, J. G. Robertson, A. Wang, S. Han, J. R. Wetterau, E. B. Janovitz, O. P. Flint, J. M. Whaley, W. N. Washburn. J. Med. Chem. 51, 1145 (2008). (http://dx.doi.org/10.1021/jm701272q)
• 3a. P. A. Clarke, S. Santos. Eur. J. Org. Chem. 2045 (2006). (http://dx.doi.org/10.1002/ejoc.200500964)
• 3b. T. L. B. Boivin. Tetrahedron 43, 3309 (1987). (http://dx.doi.org/10.1016/S0040-4020(01)81626-4)
• 3c. for reviews concerning the synthesis of THPs through C–O bond formation, see: I. Larrosa, P. Romea, F. Urpi. Tetrahedron 64, 2683 (2008). (http://dx.doi.org/10.1016/j.tet.2007.11.092)
• 3d. H. Fuwa. Heterocycles 85, 1255 (2012). (http://dx.doi.org/10.3987/REV-12-730)
• 4. J. Muzart. Tetrahedron 61, 5955 (2005). (http://dx.doi.org/10.1016/j.tet.2005.04.002)
• 5a. H. H. Jung, P. E. Floreancig. Org. Lett. 8, 1949 (2006). (http://dx.doi.org/10.1021/ol060574u)
• 5b. A. Aponick, C.-Y. Li, B. Biannic. Org. Lett. 10, 669 (2008). (http://dx.doi.org/10.1021/ol703002p)
• 5c. A. Aponick, C.-Y. Li, J. A. Palmes. Org. Lett. 11, 121 (2009). (http://dx.doi.org/10.1021/ol802491m)
• 5d. A. Aponick, B. Biannic. Org. Lett. 13, 1330 (2011). (http://dx.doi.org/10.1021/ol200203k)
• 5e. B. Biannic, T. Ghebreghiorpis, A. Aponick. Beilstein J. Org. Chem. 7, 802 (2011). (http://dx.doi.org/10.3762/bjoc.7.91)
• 6a. A. Guérinot, A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, J. Cossy. Org. Lett. 12, 1808 (2010). (http://dx.doi.org/10.1021/ol100422d)
• 6b. A. Guérinot, A. Serra-Muns, C. Bensoussan, S. Reymond, J. Cossy. Tetrahedron 67, 5024 (2011). (http://dx.doi.org/10.1016/j.tet.2011.03.112)
• 7. J. Štanbaský, M. Hocek, P. Kočovský. Chem. Rev. 109, 6729 (2009).
• 8a. H. Gong, R. Sinisi, M. R. Gagné. J. Am. Chem. Soc. 129, 1908 (2007). (http://dx.doi.org/10.1021/ja068950t)
• 8b. H. Gong, M. R. Gagné. J. Am. Chem. Soc. 130, 12177 (2008). (http://dx.doi.org/10.1021/ja8041564)
• 8c. S. Lemaire, I. N. Houpis, T. Xiao, J. Li, E. Digard, C. Gozlan, R. Liu, A. Gavryushin, C. Diène, Y. Wang, V. Farina, P. Knochel. Org. Lett. 14, 1480 (2012). (http://dx.doi.org/10.1021/ol300220p)
• 9. A. Guérinot, S. Reymond, J. Cossy. Angew. Chem., Int. Ed. 46, 6521 (2007). (http://dx.doi.org/10.1002/anie.200702206)
• 10. K. Wakabayashi, H. Yorimitsu, K. Oshima. J. Am. Chem. Soc. 123, 5374 (2001). (http://dx.doi.org/10.1021/ja0100423)
• 11. L. Nicolas, P. Angibaud, I. Stanfield, P. Bonnet, L. Meerpoel, S. Reymond, J. Cossy. Angew. Chem., Int. Ed. 51, 11101 (2012). (http://dx.doi.org/10.1002/anie.201204786)
• 12a. J. E. Aho, P. M. Pihko, T. K. Rissa. Chem. Rev. 105, 4406 (2005). (http://dx.doi.org/10.1021/cr050559n)
• 12b. S. E. Denmark, C. S. Regens, T. Kobayashi. J. Am. Chem. Soc. 129, 2774 (2007). (http://dx.doi.org/10.1021/ja070071z)
• 12c. J. Sperry, Z. E. Wilson, D. C. K. Rathwell, M. A. Brimble. Nat. Prod. Rep. 27, 1117 (2010). (http://dx.doi.org/10.1039/b911514p)
• 13a. S. A. Rizvi, D. S. Courson, V. A. Keller, R. S. Rock, S. A. Kozmin. Proc. Natl. Acad. Sci. USA 105, 4088 (2008). (http://dx.doi.org/10.1073/pnas.0710727105)
• 13b. A. V. Statsuk, R. Bai, J. L. Baryza, V. A. Verma, E. Hamel, P. A. Wender, S. A. Kozmin. Nat. Chem. Biol. 1, 383 (2005). (http://dx.doi.org/10.1038/nchembio748)
• 13c. J.-F. Biard, C. Roussakis, J.-M. Kornprobst, D. Gouiffes-Barbin, J.-F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus. J. Nat. Prod. 57, 1336 (1994). (http://dx.doi.org/10.1021/np50112a002)
• 14. A. A. Stierle, D. B. Stierle, K. Kelly. J. Org. Chem. 71, 5357 (2006). (http://dx.doi.org/10.1021/jo060018d)
• 15. A. N. Butkevich, A. Corbu, L. Meerpoel, I. Stansfield, P. Angibaud, P. Bonnet, J. Cossy. Org. Lett. 14, 4998 (2012). (http://dx.doi.org/10.1021/ol302088w)
• 16a. K. Fugami, N. Hagiwara, T. Okeda, M. Kosugi. Chem. Lett. 81 (1998). (http://dx.doi.org/10.1246/cl.1998.81)
• 16b. X. Li, A. R. Chianese, T. Vogel, R. H. Crabtree. Org. Lett. 7, 5437 (2005). (http://dx.doi.org/10.1021/ol052186i)
• 16c. B. A. Messerle, K. Q. Vuong. Organometallics 26, 3031 (2007). (http://dx.doi.org/10.1021/om061106r)
• 16d. Y. Zhang, J. Xue, Z. Xin, Z. Xie, Y. Li. Synlett 940 (2008).
• 16e. S. Selvaratnam, J. H. H. Ho, P. B. Huleatt, B. A. Messerle, C. L. L. Chai. Tetrahedron Lett. 50, 1125 (2009). (http://dx.doi.org/10.1016/j.tetlet.2008.12.075)
• 16f. C. L. L. Chai. Tetrahedron Lett. 50, 1125 (2009).
• 16g. J. H. H. Ho, R. Hodgson, J. Wagler, B. A. Messerle. Dalton Trans. 39, 4062 (2010). (http://dx.doi.org/10.1039/b926773e)
• 16h. J. H. H. Ho, S. W. S. Choy, S. A. Macgregor, B. A. Messerle. Organometallics 30, 5978 (2011). (http://dx.doi.org/10.1021/om2007826)
• 17a. S. Denmark, L. Neuville. Org. Lett. 2, 3221 (2000). (http://dx.doi.org/10.1021/ol0064112)
• 17b. J. M. Wurst, G. Liu, D. S. Tan. J. Am. Chem. Soc. 133, 7916 (2011). (http://dx.doi.org/10.1021/ja201249c)
• 17c. J. S. Potuzak, S. B. Moilanen, D. S Tan. J. Am. Chem. Soc. 127, 13796 (2005). (http://dx.doi.org/10.1021/ja055033z)
• 17d. E. Dubois, J.-M. Beau. J. Chem. Soc., Chem. Commun. 1191 (1990). (http://dx.doi.org/10.1039/c39900001191)
• 17e. D. A. Elsley, D. MacLeod, J. A. Miller, P. Quayle, G. M. Davies. Tetrahedron Lett. 33, 409 (1992). (http://dx.doi.org/10.1016/S0040-4039(00)74144-X)
• 18a. Z. Sun, G. A. Winschel, A. Borovika, P. Nagorny. J. Am. Chem. Soc. 134, 8074 (2012). (http://dx.doi.org/10.1021/ja302704m)
• 18b. I. Čorić, B. List. Nature 483, 315 (2012). (http://dx.doi.org/10.1038/nature10932)
• 19. A. Butkevich, A. Corbu, L. Meerpoel, I. Stansfield, P. Angibaud, P. Bonnet, J. Cossy. Org. Lett. 14, 4998 (2012). (http://dx.doi.org/10.1021/ol302088w)