Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1643-1650
http://dx.doi.org/10.1351/PAC-CON-11-10-25
Published online 2012-05-02
Total synthesis of gelsemoxonine
References
- 1. For reviews of Gelsemium alkaloids, see.
- 1a. J. E. Saxton. In The Alkaloids, R. H. F. Manske (Ed.), pp. 93–117, Academic Press, New York (1965).
- 1b. J. S. Bindra. In The Alkaloids, R. H. F. Manske (Ed.), pp. 83–121, Academic Press, New York (1973).
- 1c. Z.-J. Liu, R.-R. Lu. In The Alkaloids, A. Brossi (Ed.), pp. 83–140, Academic Press, San Diego (1988).
- 1d. J. E. . Nat. Prod. Rep. 9, 393 (1992). (http://dx.doi.org/10.1039/np9920900393)
- 1d. H. Takayama, S. Sakai. In The Alkaloids, G. A. Cordell (Ed.), pp. 1–78, Academic Press, New York (1997). (http://dx.doi.org/10.1039/np9920900393)
- 2. S. W. , R. J. Doll. Tetrahedron Lett. 20, 3275 (1979). (http://dx.doi.org/10.1016/S0040-4039(01)95383-3)
- 3. N. K. . J. Chem. Soc., Chem. Commun. 102 (1990). (http://dx.doi.org/10.1039/c39900000102)
- 4. A. S. , M. J. Luzzio, J. S. Mendoza. J. Org. Chem. 55, 918 (1990). (http://dx.doi.org/10.1021/jo00290a023)
- 5. W. G. , R. M. Fieseler, F. P. J. T. Rutjes, H. Hiemstra. J. Org. Chem. 65, 8317 (2000). (http://dx.doi.org/10.1021/jo001119t)
- 6. L.-Z. , G. A. Cordell, C.-Z. Ni, J. Clardy. Phytochemistry 30, 1311 (1991). (http://dx.doi.org/10.1016/S0031-9422(00)95223-3)
- 7. M. , N. Kogure, K. Yamaguchi, H. Takayama, N. Aimi. Org. Lett. 5, 2075 (2003). (http://dx.doi.org/10.1021/ol0344725)
- 8a. For a review, see: T. Hudlicky, R. Fan, J. W. Reed, K. G. Gadamasetti. In Organic Reactions, L. A. Paquette (Ed.), pp. 1–133, John Wiley, New York City (1992).
- 8b. E. , G. L. Jung, N. Moss. Tetrahedron Lett. 25, 3959 (1984). (http://dx.doi.org/10.1016/0040-4039(84)80040-4)
- 8c. A. , G. Sinai-Zingde, M. Natchus, T. Hudlicky. Tetrahedron Lett. 28, 167 (1987). (http://dx.doi.org/10.1016/S0040-4039(00)95677-6)
- 9a. O. , P. Bukowski, B. Szechner, Z. Zwierzchowska, A. Zamojski. Tetrahedron 27, 1973 (1971). (http://dx.doi.org/10.1016/S0040-4020(01)98229-8)
- 9b. V. , E. Couladouros, M. Georgiadis, G. Kokotos, T. Georgiadis. Carbohydr. Res. 222, 163 (1991). (http://dx.doi.org/10.1016/0008-6215(91)89015-8)
- 10. M. , A. D. Cuiper, H. van der Deen, R. M. Kellogg, B. L. Feringa. Tetrahedron Lett. 38, 1655 (1997). (http://dx.doi.org/10.1016/S0040-4039(97)00155-X)
- 11. Candida rugosa is synonymous with Candida cylindracea mentioned in ref. [6].
- 12. K. , H. Oyamada, M. Takase, A. Ookawa. Bull. Chem. Soc. Jpn. 57, 1948 (1984). (http://dx.doi.org/10.1246/bcsj.57.1948)
- 13a. Y. , M. Shimada. Chem. Lett. 1771 (1987). (http://dx.doi.org/10.1246/cl.1987.1771)
- 13b. Y. , M. Shimada, K. Matsumoto. Heterocycles 37, 293 (1994). (http://dx.doi.org/10.3987/COM-93-S1)
- 14. Y. , K. Shimonishi, Y. Sakakura, S. Okada, N. Aso, Y. Tanabe. Synthesis 1633 (1999). (http://dx.doi.org/10.1055/s-1999-3561)
- 15. M. , O. K. Ahmad. J. Org. Chem. 72, 1838 (2007). (http://dx.doi.org/10.1021/jo062325p)
- 16. T. , K. Hagiya. Chem. Lett. 36, 566 (2007). (http://dx.doi.org/10.1246/cl.2007.566)
- 17. A similar transformation via the NHC-catalyzed reaction is known.
- 17a. C. , F. Glorius. Angew. Chem., Int. Ed. 43, 6205 (2004). (http://dx.doi.org/10.1002/anie.200461572)
- 17b. S. S. , E. L. Rosen, J. W. Bode. J. Am. Chem. Soc. 126, 14370 (2004). (http://dx.doi.org/10.1021/ja044714b)
- 17c. A. , K. A. Scheidt. Org. Lett. 7, 905 (2005). (http://dx.doi.org/10.1021/ol050100f)
- 18a. H. , M. Hayashi. Tetrahedron Lett. 43, 5645 (2002). (http://dx.doi.org/10.1016/S0040-4039(02)01133-4)
- 18b. S. , Y. Tsuchiya, T. Mukaiyama. Chem. Lett. 537 (1991). (http://dx.doi.org/10.1246/cl.1991.537)
- 18c. L. R. , K. M. Jensen, S. M. Heilmann, J. K. Rasmussen, L. E. Lynch. Synth. Commun. 16, 617 (1986). (http://dx.doi.org/10.1080/00397918608057730)
- 19a. F. E. , R. V. Nelson, T.-F. Wang. Tetrahedron Lett. 21, 2125 (1980). (http://dx.doi.org/10.1016/S0040-4039(00)78975-1)
- 19b. R. M. , G. P. Lahm, J. W. Clader. J. Org. Chem. 45, 395 (1980). (http://dx.doi.org/10.1021/jo01291a005)
- 19c. S. , H. Reichelt. Chem. Ber. 119, 1772 (1986). (http://dx.doi.org/10.1002/cber.19861190604)
- 19d. K. , S. Hünig. Chem. Ber. 119, 2590 (1986). (http://dx.doi.org/10.1002/cber.19861190817)
- 20a. H. , G. Simchen, S. Rebsdat, K. Willi, P. Horn, R. Wahl, H. Hoffmann, G. Peter. Chem. Ber. 101, 41 (1968). (http://dx.doi.org/10.1002/cber.19681010108)
- 20b. H. H. , J. L. Ives. J. Org. Chem. 50, 3573 (1985). (http://dx.doi.org/10.1021/jo00219a025)
- 21a. Z. , J. Žemlička. Collect. Czech. Chem. Commun. 24, 2378 (1959).
- 21b. Z. , J. Žemlička. Collect. Czech. Chem. Commun. 24, 2385 (1959).
- 22a. W. J. , J. K. Stille. J. Am. Chem. Soc. 108, 3033 (1986). (http://dx.doi.org/10.1021/ja00271a037)
- 22b. Y. , Y. Xu, J. Han, J. Zheng, J. Qi, T. Jiang, X. Pan, X. She. J. Org. Chem. 74, 2743 (2009). (http://dx.doi.org/10.1021/jo9000146)
- 23a. M. E. , M. A. Lyster. J. Chem. Soc., Chem. Commun. 315 (1978). (http://dx.doi.org/10.1039/c39780000315)
- 23b. G. A. , S. C. Narang, B. G. B. Gupta, R. Malhotra. Synthesis 61 (1979). (http://dx.doi.org/10.1055/s-1979-28558)
- 24. For ring-opening reactions of epoxides in protic solvents, see.
- 24a. N. , M. R. Saidi. Org. Lett. 7, 3649 (2005). (http://dx.doi.org/10.1021/ol051220q)
- 24b. Z. , Y.-T. Cui, Z.-B. Xu, J. Qu. J. Org. Chem. 73, 2270 (2008). (http://dx.doi.org/10.1021/jo702401t)
- 25. I. , T. F. Jamison. Science 317, 1189 (2007). (http://dx.doi.org/10.1126/science.1146421)
- 26. J. , T. Harada, S. Yokoshima, T. Fukuyama. J. Am. Chem. Soc. 133, 17634 (2011). (http://dx.doi.org/10.1021/ja208617c)
