• No se han encontrado resultados

In summary, the publications that were discussed herein give a comprehensive overview of the chemistry and applications of aza-Achmatowicz reactions. It has become evident from the examples that the aza-Achmatowicz products are indeed versatile building blocks that can be further functionalized using different modes of action. Furthermore the broad application of the reaction in a large number of natural product syntheses and in the synthesis of a variety of other molecules indicates its power and versatility. Finally, although various methods for the generation of optically pure aza-Achmatowicz substrates have been reported, only a few are catalytic.

2.7 References

[1] P. S. Bailey, Ozonation in Organic Chemistry, Vol. 39-II, Academic Press, Inc. , New York, 1982.

[2] M. Kasai, H. Ziffer, J. Org. Chem. 1983, 48, 2346–2349.

[3] O. Achmatowicz Jr., P. Bukowski, B. Szechner, Z. Zwierzchowska, A. Zamojski, Tetrahedron 1971, 27, 1973–1996.

[4] (a) Y. Lefebvre, Tetrahedron Lett. 1972, 133–136. (b) Lalibert.R, G. Medawar, Y. Lefebvre, J. Med. Chem. 1973, 16, 1084–1089.

[5] (a) N. Clauson-Kaas, N. Elming, Z. Tyle, Acta Chem. Scand. 1955, 9, 1–8. (b) J. T. Nielsen, N. Elming, N. Clauson-Kaas, Acta Chem. Scand. 1955, 9, 9–13. (c) N. Clauson-Kaas, P. Nedenskov, Acta Chem. Scand. 1955, 9, 14–16. (d) P. Nedenskov, N. Elming, J. T. Nielsen, N. Clauson-Kaas, Acta Chem. Scand. 1955, 9, 17–22. (e) N. Elming, N. Clauson-Kaas, Acta Chem. Scand. 1955, 9, 23–26.

[6] (a) T. Shono, Y. Matsumura, K. Tsubata, J. Takata, Chem. Lett. 1981, 10, 1121–1124. (b) T. Shono, Y. Matsumura, K. Tsubata, K. Inoue, R. Nishida, Chem. Lett. 1983, 21– 24. (c) Y. H. Kuo, K. S. Shih, Chem. Pharm. Bull. 1991, 39, 181–183. (d) C. Muller, V. Diehl, F. W. Lichtenthaler, Tetrahedron 1998, 54, 10703–10712.

[7] M. A. Ciufolini, C. Y. Wood, Tetrahedron Lett. 1986, 27, 5085–5088.

O H O HO N H O HO CO 2 Me N HO OH CO2 Me alapyridaine (243) 241 242 NH4 1) L-alanine NaOH, H2O 2) H2, Ra-Ni, 5 bar 38% 13% Br2 MeOH/H2O

[8] The stereochemistry is throughout this thesis indicated by straight hashed

or bold bonds for racemic compounds, and by wedged hashed or bold bonds for enantiopure compounds.

[9] (a) W. S. Zhou, Z. H. Lu, Z. M. Wang, Tetrahedron Lett. 1991, 32, 1467-1470. (b) W. S. Zhou, Z. H. Lu, Z. M. Wang, Tetrahedron 1993, 49, 2641–2654.

[10] J. C. P. Hopman, E. Vandenberg, L. O. Ollero, H. Hiemstra, W. N. Speckamp, Tetrahedron Lett. 1995, 36, 4315–4318.

[11] L. X. Liao, Z. M. Wang, H. X. Zhang, W. S. Zhou, Tetrahedron: Asymmetry 1999, 10, 3649–3657.

[12] J. M. Harris, A. Padwa, J. Org. Chem. 2003, 68, 4371–4381.

[13] M. A. Ciufolini, T. Shimizu, S. Swaminathan, N. Xi, Tetrahedron Lett. 1997, 38, 4947–4950.

[14] M. A. Ciufolini, Q. Dong, Chem. Commun. 1996, 881–882.

[15] M. A. Ciufolini, C. Y. W. Hermann, Q. Dong, T. Shimizu, S. Swaminathan, N. Xi, Synlett 1998, 105–114.

[16] S. D. Koulocheri, S. A. Haroutounian, C. D. Apostolopoulos, R. K. Chada, E. A. Couladouros, Eur. J. Org. Chem. 1999, 1449–1453.

[17] S. D. Koulocheri, P. Magiatis, S. A. Haroutounian, J. Org. Chem. 2001, 66, 7915– 7918.

[18] F. D. Ferrari, A. J. Ledgard, R. Marquez, Tetrahedron 2011, 67, 4988–4994.

[19] S. D. Koulocheri, P. Magiatis, A. L. Skaltsounis, S. A. Haroutounian, Tetrahedron

2000, 56, 6135–6141.

[20] (a) J. M. Harris, A. Padwa, Org. Lett. 2002, 4, 2029–2031. (b) A. Padwa, A. Zanka, M. P. Cassidy, J. M. Harris, Tetrahedron 2003, 59, 4939–4944.

[21] D. P. Furkert, S. M. Husbands, Org. Lett. 2007, 9, 3769–3771.

[22] J. Ostrowski, H. J. Altenbach, R. Wischnat, D. J. Brauer, Eur. J. Org. Chem. 2003, 1104–1110.

[23] A. Kennedy, A. Nelson, A. Perry, Chem. Commun. 2005, 1646–1648.

[24] Y. Takahashi, H. Fuwa, A. Kaneko, M. Sasaki, S. Yokoshima, H. Koizumi, T. Takebe, T. Kan, T. Iwatsubo, T. Tomita, H. Natsugari, T. Fukuyama, Bioorg. Med. Chem. Lett. 2006, 16, 3813–3816.

[25] K. I. Yamada, Y. Yamamoto, M. Maekawa, K. Tomioka, J. Org. Chem. 2004, 69, 1531–1534.

[26] W. S. Zhou, Z. H. Lu, Y. M. Xu, L. X. Liao, Z. M. Wang, Tetrahedron 1999, 55, 11959–11983.

[27] X. Cong, K.-G. Liu, Q.-J. Liao, Z.-J. Yao, Tetrahedron Lett. 2005, 46, 8567–8571. [28] (a) S. D. Koulocheri, S. A. Haroutounian, Synthesis 1999, 1889–1892. (b) E. N.

Tzanetou, K. M. Kasiotis, P. Magiatis, S. A. Haroutounian, Molecules 2007, 12, 735– 744. (c) S. D. Koulocheri, S. A. Haroutounian, Tetrahedron Lett. 1999, 40, 6869– 6870. (d) S. D. Koulocheri, E. N. Pitsinos, S. A. Haroutounian, Synthesis 2002, 1707– 1710. (e) S. D. Koulocheri, P. Magiatis, A. L. Skaltsounis, S. A. Haroutounian, Tetrahedron 2002, 58, 6665–6671.

[29] (a) F. Gonzalez, S. Lesage, A. S. Perlin, Carbohydr. Res. 1975, 42, 267–274. (b) F. M. Hauser, S. R. Ellenberger, W. P. Ellenberger, Tetrahedron Lett. 1988, 29, 4939– 4942.

[30] J. Bi, V. K. Aggarwal, Chem. Commun. 2008, 120–122.

C A B C A B C A B C A B

[31] Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621– 9628.

[32] C. A. Leverett, M. P. Cassidy, A. Padwa, J. Org. Chem. 2006, 71, 8591–8601. [33] H. K. Yim, H. N. C. Wong, J. Org. Chem. 2004, 69, 2892–2895.

[34] T. C. Coombs, M. D. Lee, H. Wong, M. Armstrong, B. Cheng, W. Chen, A. F. Moretto, L. S. Liebeskind, J. Org. Chem. 2008, 73, 882–888.

[35] A. F. Moretto, L. S. Liebeskind, J. Org. Chem. 2000, 65, 7445–7455.

[36] (a) J. J. Yin, L. S. Liebeskind, J. Am. Chem. Soc. 1999, 121, 5811–5812. (b) H. C. Malinakova, L. S. Liebeskind, Org. Lett. 2000, 2, 3909–3911.

[37] D. G. Drueckhammer, C. F. Barbas, K. Nozaki, C. H. Wong, C. Y. Wood, M. A. Ciufolini, J. Org. Chem. 1988, 53, 1607–1611.

[38] R. Hodgson, T. Majid, A. Nelson, J. Chem. Soc., Perkin Trans. 1 2002, 1631–1643. [39] (a) M. L. Bushey, M. H. Haukaas, G. A. O'Doherty, J. Org. Chem. 1999, 64, 2984–

2985. (b) M. H. Haukaas, G. A. O'Doherty, Org. Lett. 2001, 3, 401–404. [40] H. Zhang, P. Xia, W. Zhou, Tetrahedron: Asymmetry 2000, 11, 3439–3448. [41] D. Shang, Y. Liu, X. Zhou, X. Liu, X. Feng, Chem. Eur. J. 2009, 15, 3678–3681. [42] M. A. Wijdeven, J. Willemsen, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2010, 2831–

2844.

[43] M. A. Ciufolini, C. W. Hermann, K. H. Whitmire, N. E. Byrne, J. Am. Chem. Soc.

1989, 111, 3473–3475.

[44] (a) C. F. Yang, Y. M. Xu, L. X. Liao, W. S. Zhou, Tetrahedron Lett. 1998, 39, 9227– 9228. (b) C. F. Yang, L. X. Liao, Y. M. Xu, H. X. Zhang, P. Xia, W. S. Zhou, Tetrahedron: Asymmetry 1999, 10, 2311–2318.

[45] M. P. Cassidy, A. Padwa, Org. Lett. 2004, 6, 4029–4031.

[46] Z. H. Lu, W. S. Zhou, J. Chem. Soc., Perkin Trans. 1 1993, 593–596.

[47] (a) W. S. Zhou, W. G. Xie, Z. H. Lu, X. F. Pan, J. Chem. Soc., Perkin Trans. 1 1995, 2599–2604. (b) W. S. Zhou, W. G. Xie, Z. H. Lu, X. F. Pan, Tetrahedron Lett. 1995, 36, 1291–1294.

[48] Y. M. Xu, W. S. Zhou, Chin. J. Chem. 1998, 16, 34–44.

[49] H. X. Zhang, P. Xia, W. S. Zhou, Tetrahedron 2003, 59, 2015–2020.

[50] (a) Y. M. Xu, W. S. Zhou, Tetrahedron Lett. 1996, 37, 1461–1462. (b) Y. M. Xu, W. S. Zhou, J. Chem. Soc., Perkin Trans. 1 1997, 741–746.

[51] H. J. Altenbach, R. Wischnat, Tetrahedron Lett. 1995, 36, 4983–4984.

[52] N. Matzanke, R. J. Gregg, S. M. Weinreb, M. Parvez, J. Org. Chem. 1997, 62, 1920– 1921.

[53] R. Hodgson, A. Kennedy, A. Nelson, A. Perry, Synlett 2007, 1043–1046.

[54] (a) D. Zim, V. R. Lando, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049–3051. (b) X. Y. Fu, S. Y. Zhang, J. G. Yin, T. L. McAllister, S. A. Jiang, C. H. Tann, T. K. Thiruvengadam, F. C. Zhang, Tetrahedron Lett. 2002, 43, 573–576.

[55] I. Husain, M. Saquib, V. Bajpai, B. Kumar, A. K. Shaw, J. Org. Chem. 2011, 76, 8930–8943.

[56] S. Claessens, J. Jacobs, N. De Kimpe, Synlett 2007, 741–744.

[57] N. R. Curtis, R. G. Ball, J. J. Kulagowski, Tetrahedron Lett. 2006, 47, 2635–2638. [58] (a) K. M. Peese, D. Y. Gin, Org. Lett. 2005, 7, 3323–3325. (b) K. M. Peese, D. Y.

Gin, Chem. Eur. J. 2008, 14, 1654–1665.

[59] R. Villard, F. Robert, I. Blank, G. Bernardinelli, T. Soldo, T. Hofmann, J. Agric. Food Chem. 2003, 51, 4040–4045.

C

CHHAAPPTTEERR 33

E

ENNAANNTTIIOOPPUURREE BBUUIILLDDIINNGG

B