Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1567-1574
http://dx.doi.org/10.1351/PAC-CON-11-09-06
Published online 2012-02-28
Spiroketals: Toward the synthesis of 39‑oxobistramide K
References
- 1a. C. Chem. Rev. 104, 6217 (2004). ( , J. Legros, J. Le Paih, L. Zani. http://dx.doi.org/10.1021/cr040664h)
- 1b. C.-L. Chem. Rev. 111, 1293 (2011). ( , B.-J. Li, Z.-J. Shi. http://dx.doi.org/10.1021/cr100198w)
- 2. B. T. J. Nat. Prod. 72, 1338 (2009). ( , S. Cao, P. Brodie, J. Maharavo, H. Andriamanantoanina, P. Ravelonandro, D. G. Kingston. http://dx.doi.org/10.1021/np900072k)
- 3a. F. Chem. Rev. 89, 1617 (1989). ( , K. F. Albizati. http://dx.doi.org/10.1021/cr00097a015)
- 3b. M. T. Chem. Rev. 95, 789 (1995). ( , W. Kitching. http://dx.doi.org/10.1021/cr00036a001)
- 3c. M. F. Curr. Org. Chem. 2, 395 (1998). , W. Kitching.
- 3d. S. Molecules 13, 2570 (2008). ( , P. Vogel, S. Gerber-Lemaire. http://dx.doi.org/10.3390/molecules13102570)
- 4a. A. F. Heterocycles 24, 1699 (1986). ( . http://dx.doi.org/10.3987/R-1986-06-1699)
- 4b. V. Vaillancourt, N. E. Pratt, K. F. Albizati. The Total Synthesis of Natural Products, John Wiley, New York (1992).
- 4c. K. T. Curr. Org. Chem. 7, 227 (2003). ( , B. N. Brewer. http://dx.doi.org/10.2174/1385272033372969)
- 4d. M. A. Curr. Org. Chem. 7, 1461 (2003). ( , D. P. Furkert. http://dx.doi.org/10.2174/1385272033486404)
- 4e. J. E. Chem. Rev. 105, 4406 (2005). ( , P. M. Pihko, T. K. Rissa. http://dx.doi.org/10.1021/cr050559n)
- 4f. G. Org. Biomol. Chem. 4, 1977 (2006). ( , L.‑G. Milroy, S. V. Ley. http://dx.doi.org/10.1039/b603015g)
- 4g. B. R. Molecules 13, 1942 (2008). ( , A. K. Saikia. http://dx.doi.org/10.3390/molecules13081942)
- 5. D. Org. Lett. 7, 1813 (2005). ( , J. Liu, T. Müller, L. A. Paquette. http://dx.doi.org/10.1021/ol0504291)
- 6. N. Helv. Chim. Acta 75, 604 (1992). ( , S. Goldstein, P. Deslongchamps. http://dx.doi.org/10.1002/hlca.19920750217)
- 7. J. Org. Biomol. Chem. 8, 29 (2010). ( , Y.-C. Liu, M. A. Brimble. http://dx.doi.org/10.1039/b916041h)
- 8. I. Tetrahedron Lett. 38, 8911 (1997). ( , D. J. Wallace, K. R. Gibson. http://dx.doi.org/10.1016/S0040-4039(97)10483-X)
- 9. R. E. J. Am. Chem. Soc. 110, 5768 (1988). ( , S. Thaisrivongs, P. H. Dussault. http://dx.doi.org/10.1021/ja00225a031)
- 10a. H. Org. Lett. 10, 2549 (2008). ( , M. Sasaki. http://dx.doi.org/10.1021/ol800815t)
- 10b. E. B. Org. Lett. 4, 3719 (2002). ( , W. R. Roush. http://dx.doi.org/10.1021/ol0266875)
- 11a. W. J. Chem. Soc., Chem. Commun. 855 (1986). ( , J. A. Lewis, M. T. Fletcher, J. J. De Voss, R. A. I. Drew, C. J. Moore. http://dx.doi.org/10.1039/c39860000855)
- 11b. W. J. Org. Chem. 54, 3893 (1989). ( , J. A. Lewis, M. V. Perkins, R. Drew, C. J. Moore, V. Schurig, W. A. König, W. Francke. http://dx.doi.org/10.1021/jo00277a028)
- 12a. K. Pure Appl. Chem. 55, 1845 (1983). ( . http://dx.doi.org/10.1351/pac198355111845)
- 12b. C. V. J. Org. Chem. 74, 2842 (2009). ( , S. B. Suryawanshi, R. G. Gonnade. http://dx.doi.org/10.1021/jo802539z)
- 13a. S. J. Am. Chem. Soc. 127, 9976 (2005). ( , E. Genin, V. Michelet, J.-P. Genêt. http://dx.doi.org/10.1021/ja0530671)
- 13b. Y. Angew. Chem., Int. Ed. 46, 279 (2007). ( , F. Zhou, C. J. Forsyth. http://dx.doi.org/10.1002/anie.200601963)
- 13c. Y. Synlett 940 (2008). , J. Xue, Z. Xin, Z. Xie, Y. Li.
- 13d. A. Org. Lett. 11, 121 (2009). ( , C.-Y. Li, J. A. Palmes. http://dx.doi.org/10.1021/ol802491m)
- 14. B. Org. Lett. 8, 4907 (2006). ( , J. K. De Brabander. http://dx.doi.org/10.1021/ol0619819)
- 15a. X. Org. Lett. 7, 5437 (2005). ( , A. R. Chianese, T. Vogel, R. H. Crabtree. http://dx.doi.org/10.1021/ol052186i)
- 15b. B. A. Pure Appl. Chem. 78, 385 (2006). ( , K. Q. Vuong. http://dx.doi.org/10.1351/pac200678020385)
- 15c. S. Tetrahedron Lett. 50, 1125 (2009). ( , J. H. H. Ho, P. B. Huleatt, B. A. Messerle, C. L. L. Chai. http://dx.doi.org/10.1016/j.tetlet.2008.12.075)
- 16. B. Tetrahedron Lett. 46, 6195 (2005). ( , M. S. M. Timmer, G. A. van de Marel, H. S. Overkleeft. http://dx.doi.org/10.1016/j.tetlet.2005.07.073)
- 17a. T. Org. Lett 2, 2153 (2000). ( , T. Masuda, K. Hiramoto, T. Nakata. http://dx.doi.org/10.1021/ol0060634)
- 17b. P. M. Org. Lett. 6, 3849 (2004). ( , J. E. Aho. http://dx.doi.org/10.1021/ol048321t)
- 18. A. Org. Lett. 12, 1808 (2010). ( , A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, J. Cossy. http://dx.doi.org/10.1021/ol100422d)
- 19a. D. Toxicon 26, 1129 (1988); for isolation of bistramide A, see. ( , M. Jugé, N. Grimaud, L. Welin, Y. Barbin, D. Laurent, C. Roussakis, J. P. Hénichart, J. F. Verbist. http://dx.doi.org/10.1016/0041-0101(88)90297-8)
- 19b. D. Gouiffès, S. Moreau, N. Helbecque, J. L. Bernier, J. P. Hénichart, Y. Barbin, D. Laurent, J. F. Verbist. Tetrahedron 44, 451 (1988) and cited refs.; for isolation of bistratenes, which were deduced to be identical with bistramides, see.
- 19c. B. M. J. Med. Chem. 32, 1354 (1989). ( , C. J. Hawkins, M. F. Lavin, E. J. McCaffrey, D. L. Parry, D. J. Watters. http://dx.doi.org/10.1021/jm00126a035)
- 20. For isolation of bistramides A–D and K, see.
- 20a. J. F. J. Nat. Prod. 57, 1336 (1994); for isolation of bistramides D, K, and L, see. ( , C. Roussakis, J. M. Komprobst, D. Gouiffès-Barbin, J. F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus. http://dx.doi.org/10.1021/np50112a002)
- 20b. J. F. Biard, D. Cortadellas, C. Debitus, D. Laurent, C. Roussakis, J. F. Verbist. WO 9420503 A1 (1994).
- 21. C. Eur. J. Org. Chem. 6207 (2010). ( . http://dx.doi.org/10.1002/ejoc.201000881)
- 22a. A. V. J. Am. Chem. Soc. 126, 9546 (2004). ( , D. Liu, S. A. Kozmin. http://dx.doi.org/10.1021/ja046588h)
- 22b. M. T. J. Am. Chem. Soc. 128, 4936 (2006). ( , A. C. DeBaillie. http://dx.doi.org/10.1021/ja057686l)
- 23a. A. J. Am. Chem. Soc. 114, 2321 (1992). ( , R. O. Duthaler, R. Marti, G. Rihs, P. Rhote-Streit, F. Schwarzenbach. http://dx.doi.org/10.1021/ja00033a005)
- 23b. J. Synlett 1595 (2002). ( , S. Bouzbouz, F. Pradaux, C. Willis, V. Bellosta. http://dx.doi.org/10.1055/s-2002-34233)
- 24. M. D. Varney, W. H. Romines, C. L. Palmer. U.S. Patent 5,594,139 (20 pp.), Filed 28 July 1994, Issued 14 January 1997.
- 25. F. J. Org. Chem. 57, 1722 (1992). ( , D. S. H. L. Kim, E. Rodriguez. http://dx.doi.org/10.1021/jo00032a024)
- 26. Allyl acetate 9 was prepared from benzaldehyde via a two-step sequence: a Grignard addition of vinylmagnesium bromide then the acetylation of the obtained alcohol. Procedure inspired by the literature: N. Org. Lett. 9, 2653 (2007). ( , R. Gealageas, S. P. Nolan. http://dx.doi.org/10.1021/ol070843w)
- 27a. M. Org. Lett. 1, 953 (1999). ( , S. Ding, C. W. Lee, R. H. Grubbs. http://dx.doi.org/10.1021/ol990909q)
- 27b. S. B. J. Am. Chem. Soc. 122, 8168 (2000). ( , J. S. Kingsbury, B. L. Gray, A. H. Hoveyda. http://dx.doi.org/10.1021/ja001179g)
- 28. Compound 12 was prepared according to the following synthetic sequence: benzylation.
- 28a. U. Synthesis 568 (1987); ester reduction. ( . http://dx.doi.org/10.1055/s-1987-28007)
- 28b. J. D. J. Org. Chem. 57, 5292 (1992); bromination. ( , M. Kawasaki. http://dx.doi.org/10.1021/jo00046a008)
- 28c. G.-J. Tetrahedron 51, 5417 (1995); preparation of phosphonium salt. ( , J. A. Clase, J. C. Lennon, S. V. Ley, J. Staunton. http://dx.doi.org/10.1016/0040-4020(95)00201-I)
- 28d. J. T. Org. Lett. 9, 327 (2007). ( , I. E. Wrona, J. S. Panek. http://dx.doi.org/10.1021/ol062957y)
- 29. Keto-phosphonate 15 was prepared according to the literature procedure: B. Synthesis 1048 (1985). ( , L. Medinger, J.-P. Haelters, G. Sturtz. http://dx.doi.org/10.1055/s-1985-31424)
- 30. M. G. J. Org. Chem. 63, 1221 (1998). ( , S. Ramurthy, M. J. Miller. http://dx.doi.org/10.1021/jo971772p)