Pure and Applied Chemistry

Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 461-478

http://dx.doi.org/10.1351/PAC-CON-10-10-19

Published online 2011-01-29

1,5-Polyols: Challenging motifs for configurational assignment and synthesis

References

• 1. S. E. Bode, M. Wolberg, M. Muller. Synthesis 557 (2006).
• 2. Review: D. B. Kimball, L. A. Silks. Curr. Org. Chem. 10, 1975 (2006). (http://dx.doi.org/10.2174/138527206778521268)
• 3. Isolation, structure, and biological activity.
• 3a. T. Kamiyama, T. Umino, N. Fujisaki, K. Fujimori, T. Satoh, Y. Yamashita, S. Ohshima, J. Watanabe, K. Yokose. J. Antibiot. 46, 1039 (1993).
• 3b. Y. Kobayashi, W. Czechtizky, Y. Kishi. Org. Lett. 5, 93 (2003). (http://dx.doi.org/10.1021/ol0272895)
• 3c. T. Satoh, W. C. Kouns, Y. Yamashita, T. Kamiyama, B. Steiner. Biochem. J. 301, 785 (1994).
• 4. G.-S. Kim, L. Zeng, F. Alali, L. L. Rogers, F.-E. Wu, J. L. McLaughlin, S. Sastrodihardjo. J. Nat. Prod. 61, 432 (1998). (http://dx.doi.org/10.1021/np970534m)
• 5. A. Bermejo, B. Figadere, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes. Nat. Prod. Rep. 22, 269 (2005). (http://dx.doi.org/10.1039/b500186m)
• 6. Isolation, structure, and biological activity.
• 6a. M. Satake, M. Murata, T. Yasumoto, T. Fujita, H. Naoki. J. Am. Chem. Soc. 113, 9859 (1991). (http://dx.doi.org/10.1021/ja00026a027)
• 6b. M. Murata, S. Matsuoka, N. Matsumori, G. K. Paul, K. Tachibana. J. Am. Chem. Soc. 121, 870 (1999). (http://dx.doi.org/10.1021/ja983655x)
• 7. J. R. Deeds, D. E. Terlizzi, J. E. Adolf, D. K. Stoecker, A. R. Place. Harmful Algae 1, 169 (2002). (http://dx.doi.org/10.1016/S1568-9883(02)00027-6)
• 8. J. Peng, A. R. Place, W. Yoshida, C. Anklin, M. T. Hamann. J. Am. Chem. Soc. 132, 3277 (2010). (http://dx.doi.org/10.1021/ja9091853)
• 9. S. V. Mudur, J. B. Gloer, D. T. Wicklow. J. Antibiot. 59, 500 (2006). (http://dx.doi.org/10.1038/ja.2006.70)
• 10. Isolation, structure, and biological activity.
• 10a. Y. Hayakawa, N. Kanamaru, N. Morisaki, H. Seto. Tetrahedron Lett. 32, 213 (1991). (http://dx.doi.org/10.1016/0040-4039(91)80858-4)
• 10b. F. Tamotsu, E. Keitaro, S. Tomomitsu, H. Hiroko, O. Hirayasu, S. Noriko, F. Takeshi, N. Hideo, I. Yasuhiro. J. Antibiot. 55, 873 (2002).
• 11. H. C. Kwon, C. A. Kauffman, P. R. Jensen, W. Fenical. J. Am. Chem. Soc. 128, 1622 (2006). (http://dx.doi.org/10.1021/ja0558948)
• 12. H. C. Kwon, C. A. Kauffman, P. R. Jensen, W. Fenical. J. Org. Chem. 74, 675 (2009). (http://dx.doi.org/10.1021/jo801944d)
• 13. S. D. Rychnovsky, B. N. Rogers, T. I. Richardson. Acc. Chem. Res. 31, 9 (1998). (http://dx.doi.org/10.1021/ar960223n)
• 14. D. P. Curran, Q. Zhang, H. Lu, V. Gudipati. J. Am. Chem. Soc. 128, 9943 (2006). (http://dx.doi.org/10.1021/ja062469l)
• 15. P. Cai, F. Kong, P. Fink, M. E. Ruppen, R. T. Williamson, T. Keibo. J. Nat. Prod. 70, 215 (2007). (http://dx.doi.org/10.1021/np060542f)
• 16. Y. Kobayashi, C. H. Tan, Y. Kishi. Helv. Chim. Acta 83, 2562 (2000). (http://dx.doi.org/10.1002/1522-2675(20000906)83:9<2562::AID-HLCA2562>3.0.CO;2-Z)
• 17. Review: J. M. Seco, E. Quinoa, R. Riguera. Chem. Rev. 104, 17 (2004). (http://dx.doi.org/10.1021/cr000665j)
• 18. J. Peng, A. R. Place, W. Yoshida, C. Anklin, M. T. Hamann. J. Am. Chem. Soc. 132, 3277 (2010). (http://dx.doi.org/10.1021/ja9091853)
• 19. M. Murata, S. Matsuoka, N. Matsumori, G. K. Paul, K. Tachibana. J. Am. Chem. Soc. 121, 870 (1999). (http://dx.doi.org/10.1021/ja983655x)
• 20a. H. Seike, I. Ghosh, Y. Kishi. Org. Lett. 8, 3861 (2006). (http://dx.doi.org/10.1021/ol061580t)
• 20b. H. Seike, I. Ghosh, Y. Kishi. Org. Lett. 8, 3865 (2006). (http://dx.doi.org/10.1021/ol061582d)
• 20c. S. Higashibayashi, Y. Kishi. Tetrahedron 60, 11977 (2004). (http://dx.doi.org/10.1016/j.tet.2004.08.101)
• 20d. Y. Kobayashi, N. Hayashi, Y. Kishi. Tetrahedron Lett. 44, 7489 (2003). (http://dx.doi.org/10.1016/j.tetlet.2003.08.022)
• 20e. S. Fidanze, F. Song, M. Szlosek-Pinaud, P. L. C. Small, Y. Kishi. J. Am. Chem. Soc. 123, 10117 (2001). (http://dx.doi.org/10.1021/ja011824z)
• 20f. Y. Kobayashi, N. Hayashi, C. H. Tan, Y. Kishi. Org. Lett. 3, 2245 (2001). (http://dx.doi.org/10.1021/ol010108z)
• 20g. Y. Kobayashi, C. H. Tan, Y. Kishi. J. Am. Chem. Soc. 123, 2076 (2001). (http://dx.doi.org/10.1021/ja004154q)
• 20h. Y. Kobayashi, C. H. Tan, Y. Kishi. Helv. Chim. Acta 83, 2562 (2000). (http://dx.doi.org/10.1002/1522-2675(20000906)83:9<2562::AID-HLCA2562>3.0.CO;2-Z)
• 20i. Y. Kobayashi, J. Lee, K. Tezuka, Y. Kishi. Org. Lett. 1, 2177 (1999). (http://dx.doi.org/10.1021/ol9903786)
• 20j. J. Lee, Y. Kobayashi, K. Tezuka, Y. Kishi. Org. Lett. 1, 2181 (1999). (http://dx.doi.org/10.1021/ol990379y)
• 21. Y. Kobayashi, W. Czechtizky, Y. Kishi. Org. Lett. 5, 93 (2003). (http://dx.doi.org/10.1021/ol0272895)
• 22. J. B. MacMillan, T. F. Molinski. J. Am. Chem. Soc. 126, 9944 (2004). (http://dx.doi.org/10.1021/ja047741a)
• 23. D. S. Dalisay, T. Quach, T. F. Molinski. Org. Lett. 12, 1524 (2010). (http://dx.doi.org/10.1021/ol100249v)
• 24a. P. Kumar, E. J. Thomas, D. Tray. Tetrahedron 63, 6287 (2007). (http://dx.doi.org/10.1016/j.tet.2007.03.070)
• 24b. S. Donnelly, E. J. Thomas, E. A. Arnott. Chem. Commun. 1460 (2003). (http://dx.doi.org/10.1039/b303151a)
• 24c. R. J. Maguire, E. J. Thomas. J. Chem. Soc., Perkin Trans. 1 2477 (1995). (http://dx.doi.org/10.1039/p19950002477)
• 25. A. Hafner, R. O. Duthaler, R. Marti, J. Rihs, P. Rothe-Streit, F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992). (http://dx.doi.org/10.1021/ja00033a005)
• 26. S. BouzBouz, J. Cossy. Org. Lett. 3, 1451 (2001). (http://dx.doi.org/10.1021/ol0157095)
• 27. S. BouzBouz, J. Cossy. Org. Lett. 6, 3469 (2004). (http://dx.doi.org/10.1021/ol048862i)
• 28. Review: H. C. Brown, P. V. Ramachandran. J. Organomet. Chem. 500, 1 (1995). (http://dx.doi.org/10.1016/0022-328X(95)00509-O)
• 29. W. R. Roush, A. E. Walts, L. K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985). (http://dx.doi.org/10.1021/ja00312a062)
• 30. E. Fernandez, J. Pietruszka, W. Frey. J. Org. Chem. 75, 5580 (2010). (http://dx.doi.org/10.1021/jo1008959)
• 31. H. C. Brown, G. Narla. J. Org. Chem. 60, 4686 (1995). (http://dx.doi.org/10.1021/jo00120a005)
• 32. E. M. Flamme, W. R. Roush. J. Am. Chem. Soc. 124, 13644 (2002). (http://dx.doi.org/10.1021/ja028055j)
• 33. E. M. Flamme, W. R. Roush. Org. Lett. 7, 1411 (2005). (http://dx.doi.org/10.1021/ol050250q)
• 34. T. Oishi, M. Kanemoto, R. Swasono, N. Matsumori, M. Murata. Org. Lett. 10, 5203 (2008). (http://dx.doi.org/10.1021/ol802168r)
• 35a. R. Lira, W. R. Roush. Org. Lett. 9, 533 (2007). (http://dx.doi.org/10.1021/ol0629869)
• 35b. F. Li, W. R. Roush. Org. Lett. 11, 2932 (2009). (http://dx.doi.org/10.1021/ol9009877)
• 36. H. Y. Cho, J. P. Morken. J. Am. Chem. Soc. 132, 7576 (2010). (http://dx.doi.org/10.1021/ja101513d)
• 37. L. Paquette, S.-K. Chang. Org. Lett. 7, 3111 (2005). (http://dx.doi.org/10.1021/ol0511833)
• 38a. K. Zhang, D. P. Curran. Synlett 667 (2010).
• 38b. V. Gudipati, R. Bajpai, D. P. Curran. Collect. Czech. Chem. Commun. 74, 774 (2009).
• 38c. V. Gudipati. Ph.D. thesis, University of Pittsburgh (2008).
• 39. G. K. Friestad, G. Sreenilayam. Org. Lett. 12, 5016 (2010). (http://dx.doi.org/10.1021/ol1021417)
• 40. Reviews.
• 40a. C. Aissa. Eur. J. Org. Chem. 1831 (2009). (http://dx.doi.org/10.1002/ejoc.200801117)
• 40b. P. R. Blakemore. J. Chem. Soc., Perkin Trans. 1 2563 (2002). (http://dx.doi.org/10.1039/b208078h)
• 41. Representative examples of Julia–Kocienski couplings in recent natural product syntheses.
• 41a. S. Hanessian, T. Focken, R. Oza. Org. Lett. 12, 3172 (2010). (http://dx.doi.org/10.1021/ol101103q)
• 41b. A. K. Ghosh, H. Yuan. Org. Lett. 12, 3120 (2010). (http://dx.doi.org/10.1021/ol101105v)
• 41c. A. B. Smith, S. Dong, J. B. Brenneman, R. J. Fox. J. Am. Chem. Soc. 131, 12109 (2009). (http://dx.doi.org/10.1021/ja906115a)
• 41d. J. D. Panarese, S. P. Waters. Org. Lett. 11, 5086 (2009). (http://dx.doi.org/10.1021/ol902154p)
• 41e. M. E. Jung, G.-Y. J. Im. J. Org. Chem. 74, 8739 (2009). (http://dx.doi.org/10.1021/jo902029x)
• 42. See ref. [34].
• 43. K. Leijondahl, L. Boren, R. Braun, J.-E. Bäckvall. Org. Lett. 10, 2027 (2008). (http://dx.doi.org/10.1021/ol800468h)
• 44a. A. B. Smith, A. M. Boldi. J. Am. Chem. Soc. 119, 6925 (1997). (http://dx.doi.org/10.1021/ja970371o)
• 44b. A. B. Smith, C. M. Adams. Acc. Chem. Res. 37, 365 (2004). (http://dx.doi.org/10.1021/ar030245r)
• 45. A. B. Smith, M. Xian. J. Am. Chem. Soc. 128, 66 (2006). (http://dx.doi.org/10.1021/ja057059w)