Anionic Cyclization Reactions

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Reviews:

Myers Anionic Cyclization Reactions Chem 115
Mal, D.; Pahari, P. Chem. Rev. 2007, 107, 1892–1918.
Rathwell, K.; Brimble, M. Synthesis 2007, 643–662.
Mitchell, A. S.; Russell, R. A. Tetrahedron 1995, 51, 5207–5236.

Generalized Reaction Scheme

Eisenmuth, W.; Renfroe, H. B.; Schmid, H. Helv. Chim. Acta. 1965, 48, 375–379.

Hauser Annulation

Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178–180.

Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178–180

Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 25, 2213–2216.

Kraus Annulation

Kraus, G. A.; Sugimoto, H. Tetrahedron Lett. 1978, 26, 2263–2266.

Comparison of Hauser and Kraus Annulations

Hauser, F. M.; Combs, D. W. J. Org. Chem. 1980, 45, 4071–4073.

Mal, D.; Patra, A.; Roy, H. Tetrahedron Lett. 2004, 45, 7895–7898.

Li, T.-T.; Walsgrove, T. C. Tetrahedron Lett. 1981, 22, 3741–3744.

Sammes Annulation

Broom, N. J. P.; Sammes, P. G. J. Chem. Soc. Chem. Commun. 1978, 162–164.

Broom, N. J. P.; Sammes, P. G. J. Chem. Soc. Perkin Trans. 1 1981, 465–470.

Staunton-Weinreb Annulations

Dodd, J. H.; Weinreb, S. M. Tetrahedron Lett. 1979, 38, 3593–3596.

Evans, G.; Leeper, F. J.; Murphy, J. A.; Staunton, J. J. Chem. Soc. Chem. Commun. 1979, 205–206.

Leeper, F. J.; Staunton, J. J. Chem. Soc. Chem. Commun. 1979, 5, 206–207.

White, J. D.; Nolen, E. G.; Miller, C. H. J. Org. Chem. 1986, 51, 1152–1155.

Other Nucleophiles

Kraus, G. A.; Cho, H.; Crowley, S.; Roth, B.; Sugimoto, H.; Prugh, S. J. Org. Chem. 1983, 48, 3439–3944.

Hauser, F. M.; Dorsch, W. A.; Mal, D. Org. Lett. 2002, 4, 2237–2239.

Tamura, Y.; Sasho, M.; Nakagawa, K.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473–478.

Synthesis of Cyclohexanone Derivatives

Swenton Annulation

Chenard, B. L.; Anderson, D. K.; Swenton, J. S. J. Chem. Soc. Chem. Commun. 1980, 932–933.

Tamura, Y.; Sasho, M.; Nakagawa, K.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473–478.

Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y. Synthesis 1986, 785–786.

Boger, D. L.; Zhang, M. J. Org. Chem. 1992, 57, 3974–3977.

Clive, D. L. J.; Sedgeworth, J. J. Heterocyclic Chem. 1987, 24, 509–511.

Stereoselective Synthesis of Cyclohexanone Derivatives

Franck, R. W.; Bhat, V.; Subramaniam, C. S. J. Am. Chem. Soc. 1986, 108, 2455–2457.

Synthesis of bioxanthracene (–)-ES-242-4:

Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998, 39, 1771–1772.

Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913–1717927.

Carpenter, T. A.; Evans, G. E.; Leeper, F. J.; Staunton, J.; Wilkinson, M. R. J. Chem. Soc. Perkin Trans. 1 1984, 1043–1051.

Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D.; Myers, A. G. Science 2005, 308, 395–398.

Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913–1717927.

Kummer, D. A.; Li, D.; Dion, A.; Myers, A. G. Chem. Sci. 2011, 2, 1710–1718.

Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D.; Myers, A. G. Science 2005, 308, 395–398.

Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913–1717927.

White, J. D.; Demnitz, F. W. J.; Xu, Q.; Martin, W. H. C. Org. Lett. 2008, 10, 2833–2836.

Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D.; Myers, A. G. Science 2005, 308, 395–398

Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D.; Myers, A. G. Science 2005, 308, 395–398.

Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913–1717927.

Ronn, M.; Zhu, Z.; Hogan, P. C.; Zhang, W.-Y.; Niu, J.; Katz, C. E.; Dunwoody, N.; Gilicky, O.; Deng, Y.; Hunt, D. K.; He, M.; Chen, C.-L.; Sun, C.; Clark, R. B.; Xiao, X.-Y. Org. Process Res. Dev. 2013, 17, 838–845.

Examples in Synthesis

Synthesis of 1,4-Dihydroxynaphthalene Derivatives

Hauser, F. M.; Prasanna, S. J. Org. Chem. 1979, 44, 2596–2598.

Synthesis of a dideoxydynemicin analog

Myers, A. G.; Fraley, M. E.; Tom, N. J. J. Am. Chem. Soc. 1994, 116, 11556–11557.

Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33–43.

Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072–6094.

Synthesis of Trioxacarcin A

Svenda, J.; Hill, N.; Myers, A. G. Proc. Natl. Acad. Sci. 2011, 108, 6709–6714.

Magauer, T.; Smaltz, D. J.; Myers, A. G. Nat. Chem. 2013, 5, 886–893

Liau, B. B.; Milgram, B. C.; Shair, M. D. J. Am. Chem. Soc. 2012, 134, 16765–16772.

Synthesis of viridicatumtoxin B

Nicolaou, K. C.; Nielewski, C.; Hale, C. R. H.; Ioannidou, H. A.; ElMarrouni, A.; Koch, L. G. Angew. Chem. Int. Ed. 2013, 52, 8736–8741.

Synthesis of 1-Hydroxynaphthalene Derivatives

Tatsuta, K.; Yoshimoto, T.; Gunji, H.; Okado, Y.; Takahashi, M. Chem. Lett. 2000, 646–647.

Synthesis of a benanomicinone analogue

Hauser, F. M.; Liao, H.; Sun, Y. Org. Lett. 2002, 4, 2241–2243.

Shair, M. D.; Yoon, T.-Y.; Danishefsky, S. J. Angew. Chem. Int. Ed. 1995, 34, 1721–1723.

Shair, M. D.; Yoon, T.-Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509–9525.

Liau, B. B.; Milgram, B. C.; Shair, M. D. J. Am. Chem. Soc. 2012, 134, 16765–16772.

Synthesis of Annulation Substrates

Hauser Annulation Substrates

Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178–180

Hauser, F. M.; Rhee, R. P.; Prasanna, S. Synthesis 1980, 72–74.

Kraus, G. A.; Cho, H.; Crowley, S.; Roth, B.; Sugimoto, H.; Prugh, S. J. Org. Chem. 1983, 48, 3439–3444.

Hauser, F. M.; Gauuan, P. J. F. Org. Lett. 1999, 1, 671–672.

Tatsuka, K.; Inukai, T.; Itoh, S.; Kawarasaki, M.; Nakano, Y. J. Antibiot. 2002, 55, 1076–1080.

Hauser, F. M.; Dorsch, W. A. Org. Lett. 2003, 5, 3753–3754.

Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178–180

Hauser, F. M.; Rhee, R. P.; Prasanna, S. Synthesis 1980, 72–74.

Kraus Annulation Substrates

Kraus, G. A.; Sugimoto, H. Tetrahedron Lett. 1978, 26, 2263–2266.

Li, T.-T.; Wu, Y. L. J. Am. Chem. Soc. 1981, 103, 7007–7009.

Freskos, J. N.; Morrow, G. W.; Swenton, J. S. J. Org. Chem. 1985, 50, 805–810.

Kraus, G. A.; Sugimoto, H. Tetrahedron Lett. 1978, 26, 2263–2266.

Kraus, G. A.; Cho, H.; Crowley, S.; Roth, B.; Sugimoto, H.; Prugh, S. J. Org. Chem. 1983, 48, 3439–3444.

Svenda, J.; Hill, N. ; Myers, A. G. Proc. Natl. Acad. Sci. 2011, 108, 6709–6714.

Magauer, T.; Smaltz, D. J.; Myers, A. G. Nat. Chem. 2013, 5, 886–893.