Pure and Applied Chemistry

Pure Appl. Chem., 2012, Vol. 84, No. 6, pp. 1445-1453

http://dx.doi.org/10.1351/PAC-CON-11-09-10

Published online 2012-04-02

Synthesis of saxitoxins

References

• 1a. E. J. Schantz, J. D. Mold, D. W. Stanger, J. Shavel, F. J. Riel, J. P. Bowden, J. M. Lynch, R. S. Wyler, B. Riegel, H. Sommer. J. Am. Chem. Soc. 79, 5230 (1957). (http://dx.doi.org/10.1021/ja01576a044)
• 1b. W. Schuett, H. Rapoport. J. Am. Chem. Soc. 84, 2266 (1962). (http://dx.doi.org/10.1021/ja00870a056)
• 2. L. E. Llewellyn. Nat. Prod. Rep. 23, 200 (2006). (http://dx.doi.org/10.1039/b501296c)
• 3a. E. J. Schantz, V. E. Ghazarossian, H. K. Schnoes, F. M. Strong, J. P. Springer, J. O. Pezzanite, J. Clardy. J. Am. Chem. Soc. 97, 1238 (1975). (http://dx.doi.org/10.1021/ja00838a045)
• 3b. J. Bordner, W. E. Thiessen, H. A. Bates, H. Rapoport. J. Am. Chem. Soc. 97, 6008 (1975). (http://dx.doi.org/10.1021/ja00854a009)
• 4. R. S. Rogers, H. Rapoport. J. Am. Chem. Soc. 102, 7335 (1980). (http://dx.doi.org/10.1021/ja00544a030)
• 5a. F. E. Koehn, V. E. Ghazarossian, E. J. Schantz, H. K. Schnoes, F. M. Strong. Bioorg. Chem. 10, 412 (1981). (http://dx.doi.org/10.1016/0045-2068(81)90053-5)
• 5b. A. A. Genenah, Y. Shimizu. J. Agric. Food Chem. 29, 1289 (1981). (http://dx.doi.org/10.1021/jf00108a047)
• 5c. C. F. Wichmann, W. P. Niemczura, H. K. Schnoes, S. Hall, P. B. Reichardt, S. D. Darling. J. Am. Chem. Soc. 103, 6977 (1981). (http://dx.doi.org/10.1021/ja00413a042)
• 5d. E. Moczydlowski, S. Hall, S. S. Garber, G. S. Strichartz, C. J. Miller. J. Gen. Physiol. 84, 687 (1984). (http://dx.doi.org/10.1085/jgp.84.5.687)
• 5e. J. J. Sullivan, M. M. Wekell, L. L. Kentala. J. Food Sci. 50, 26 (1985). (http://dx.doi.org/10.1111/j.1365-2621.1985.tb13269.x)
• 5f. Y. Oshima. Manual on Harmful Marine Microalgae, G. Hallegraeff, D. Anderson, A. Cembella (Eds.), pp. 81–94, UNESCO, Paris (1995).
• 5g. H. Onodera, M. Satake, Y. Oshima, T. Yasumoto, W. W. Carmichael. Nat. Toxins 5, 146 (1997). (http://dx.doi.org/10.1002/19970504NT4)
• 5h. L. Llewellyn, A. Negri, M. Quilliam. Toxicon 43, 101 (2004). (http://dx.doi.org/10.1016/j.toxicon.2003.10.016)
• 5i. G. Usup, C.-P. Leaw, M.-Y. Cheah, A. Ahmad, B.-K. Ng. Toxicon 44, 37 (2004). (http://dx.doi.org/10.1016/j.toxicon.2004.03.026)
• 5j. M. Yotsu-Yamashita, Y.-H. Kim, S. C. Dudley Jr., G. Choudhary, A. Pfahnl, Y. Oshima, J. W. Daly. Proc. Natl. Acad. Sci. USA 101, 4346 (2004). (http://dx.doi.org/10.1073/pnas.0400368101)
• 6a. H. Tanino, T. Nakata, Y. Kaneko, Y. Kishi. J. Am. Chem. Soc. 99, 2818 (1977). (http://dx.doi.org/10.1021/ja00450a079)
• 6b. Y. Kishi. Heterocycles 14, 1477 (1980). (http://dx.doi.org/10.3987/R-1980-10-1477)
• 6c. S. M. Hannick, Y. Kishi. J. Org. Chem. 48, 3833 (1983). (http://dx.doi.org/10.1021/jo00169a053)
• 7a. P. A. Jacobi, M. J. Martinelli, S. Polanc. J. Am. Chem. Soc. 106, 5594 (1984). (http://dx.doi.org/10.1021/ja00331a032)
• 7b. M. J. Martinelli, A. D. Brownstein, P. A. Jacobi, S. Polanc. Cort. Chem. Acta 59, 267 (1986).
• 7c. P. A. Jacobi. Strategies and Tactics in Organic Synthesis, Vol. 2, T. Lindberg (Ed.), pp. 191–219, Academic Press, New York (1989).
• 8a. J. J. Fleming, J. Du Bois. J. Am. Chem. Soc. 128, 3926 (2006). (http://dx.doi.org/10.1021/ja0608545)
• 8b. J. J. Fleming, M. D. McReynolds, J. Du Bois. J. Am. Chem. Soc. 129, 9964 (2007). (http://dx.doi.org/10.1021/ja071501o)
• 9a. C. Y. Hong, Y. Kishi. J. Am. Chem. Soc. 114, 7001 (1992). (http://dx.doi.org/10.1021/ja00044a008)
• 9b. J. V. Mulcahy, J. Du Bois. J. Am. Chem. Soc. 130, 12630 (2008). Recently, Du Bois reported derivatization of STX.
• 9c. B. M. Andresen, J. Du Bois. J. Am. Chem. Soc. 131, 12524 (2009). (http://dx.doi.org/10.1021/ja904179f)
• 10a. Y. Sawayama, T. Nishikawa. Synlett 651 (2011).
• 10b. Y. Sawayama, T. Nishikawa. Angew. Chem. 123, 7314 (2011). (http://dx.doi.org/10.1002/ange.201102494)
• 10c. Y. Sawayama, T. Nishikawa. Angew. Chem., Int. Ed. 50, 7176 (2011). Recently, Looper also reported total synthesis of (+)-saxitoxin 1.
• 10d. V. R. Bhonde, R. E. Looper. J. Am. Chem. Soc. 133, 20172 (2011). (http://dx.doi.org/10.1021/ja2098063)
• 11a. O. Iwamoto, H. Koshino, D. Hashizume, K. Nagasawa. Angew. Chem. 119, 8779 (2007). (http://dx.doi.org/10.1002/ange.200703326)
• 11b. O. Iwamoto, H. Koshino, D. Hashizume, K. Nagasawa. Angew. Chem., Int. Ed. 46, 8625 (2007). (http://dx.doi.org/10.1002/anie.200703326)
• 11c. O. Iwamoto, R. Shinohara, K. Nagasawa. Chem. Asian J. 4, 277 (2009). (http://dx.doi.org/10.1002/asia.200800382)
• 11d. O. Iwamoto, K. Nagasawa. Org. Lett. 12, 2150 (2010). (http://dx.doi.org/10.1021/ol1006696)
• 12. P. G. Mattingly, M. J. Miller. J. Org. Chem. 45, 410 (1980). (http://dx.doi.org/10.1021/jo01291a007)
• 13. Recent review for guanidine alkaloids.
• 13a. R. G. S. Berlinck, A. C. B. Burtoloso, M. H. Kossuga. Nat. Prod. Rep. 25, 919 (2008). Selected articles.
• 13b. A. Hinman, J. Du Bois. J. Am. Chem. Soc. 125, 11510 (2003). (http://dx.doi.org/10.1021/ja0368305)
• 13c. D. Urabe, T. Nishikawa, M. Isobe. Chem. Asian J. 1, 125 (2006). (http://dx.doi.org/10.1002/asia.200600038)
• 13d. S. Wang, D. Romo. Angew. Chem. 120, 1304 (2008). (http://dx.doi.org/10.1002/ange.200703998)
• 13e. S. Wang, D. Romo. Angew. Chem., Int. Ed. 47, 1284 (2008). (http://dx.doi.org/10.1002/anie.200703998)
• 13f. T. Imaoka, O. Iwamoto, K. Noguchi, K. Nagasawa. Angew. Chem. 121, 3857 (2009). (http://dx.doi.org/10.1002/anie.200806233)
• 13f. T. Imaoka, O. Iwamoto, K. Noguchi, K. Nagasawa. Angew. Chem., Int. Ed. 48, 3799 (2009).