An efficient, PIFA mediated approach to benzo-, naphtho-, and heterocycle-fused pyrrolo[2,1-c][1,4]diazepines. An advantageous access to the antitumor antibiotic DC-81
Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, UK
Thurston, D. E. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; The Macmillan Press Ltd.: London, UK, 1993; Vol. 1, pp 54-88.
Hurley, L. H.; Reck, T.; Thurston, D. E.; Langley, D. R.; Holden, K. G.; Hertzberg, R. P.; Hoover, J. R.; Gallagher, G., Jr.; Faucette, L. F.; Mong, S.-M.; Johnson, R. K. Chem. Res. Toxicol. 1988, 1, 258-268.
(a) For a comprehensive review of different synthetic approaches to the PBD skeleton, see: Kamal, A.; Rao, M. V.; Laxman, N.; Ramesh, G.; Reddy, G. S. K. Curr. Med. Chem. Anti-Cancer Agents 2002, 2, 215-254.
(a) Thurston, D. E.; Murty, V. S.; Langley, D. R.; Jones, G. B. Synthesis 1990, 81-84. For a recent application of this approach in the synthesis of tetrahydroisoquinolino-fused benzodiazepines, see: Kothakonda, K. K.; Bose, D. S. Bioorg. Med. Chem. Lett. 2004, 14, 4371-4373.
(a) Thurston, D. E.; Murty, V. S.; Langley, D. R.; Jones, G. B. Synthesis 1990, 81-84. For a recent application of this approach in the synthesis of tetrahydroisoquinolino-fused benzodiazepines, see: Kothakonda, K. K.; Bose, D. S. Bioorg. Med. Chem. Lett. 2004, 14, 4371-4373.
(e) See, for example: Wang, T.; Lui, A. S.; Cloudsdale, I. S. Org. Lett. 1999, 1, 1835-1837. Kamal, A.; Reddy, B. S. N.; Reddy, G. S. K. Synlett 1999, 1251-1252.
(e) See, for example: Wang, T.; Lui, A. S.; Cloudsdale, I. S. Org. Lett. 1999, 1, 1835-1837. Kamal, A.; Reddy, B. S. N.; Reddy, G. S. K. Synlett 1999, 1251-1252.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
For general reviews on polyvalent iodine compounds, see: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (c) Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (e) Varvoglis, A. In Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997. (f) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458. (g) Varvoglis A. Tetrahedron 1997, 53, 1179-1255. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Ochiai, M. Chem. Hypervalent Compd. 1999, 359-387. (j) Koser, G. F. Aldrichim. Acta 2001, 34, 89-102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Wirth, T. Top. Curr. Chem. 2003, 224, 1-264.
(a) Romero has employed TFA as an additive in a PIFA-mediated oxidative cyclization of a N-methoxyamide to obtain the tetrahydroquinoline skeleton with excellent results. However, the role of TFA remains unknown. See ref 15c.
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(b) It has been proposed that the coordination of Lewis acids with the trifluoroacetoxy ligands activates the iodine(III) reagent. See: Takada, T.; Arisawa, M.; Gyoten, M.; Hamada, R.; Tohma, H.; Kita, Y. J. Org. Chem. 1998, 63, 7698-7706.
(b) The Li/DTBB-induced reduction alternative did not produce the expected results. See, for example: Yus, M.; Radivoy, G.; Alonso, F. Synthesis 2001, 6, 914-918.
(c) These substrates turned out to be unreactive toward hydrogenation using Pearlman's catalyst. See, for example: Chang, C.-Y.; Yang, T.-K. Tetrahedron: Asymmetry 2003, 14, 2081-2085.
(a) There is considerable interest in developing low molecular weight molecules with sequence selectivity DNA interactive properties as tools for molecular biology and as possible therapeutic agents to inactivate particular genes. Lown, J. W.; Kumar, R. Mini Rev. Med. Chem. 2003, 3, 323-339.
(b) It is sensible to maintain its tetrahydrogenated nature because when the PBD includes a fully unsaturated pyrrole ring the imine double bond remains unreactive toward nucleophiles showing, hence, little interest from a biological point of view. See ref 6b.
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For an alternative synthesis of 11e, see: Jolivert-Fouchet, S.; Fabis, F.; Rault, S. Tetrahedron Lett. 1998, 39, 5369-5372.
For previously reported representative syntheses of DC-81 (1) or synthetic intermediates, see: (a) Bose, D. S.; Jones, G. B.; Thurston, D. E. Tetrahedron 1992, 48, 751-758.