Synthetic and mechanistic studies on the azabicyclo[7.3.1]enediyne core and naphtho[2,3-h]quinoline portions of dynemicin A

Journal of the American Chemical Society

Volumn 119, Issue 24, 1997, Pages 5591-5605

  Magnus, Philip ^a   Eisenbeis, Shane A ^a   Fairhurst, Robin A ^a   Iliadis, Theodore ^a   Magnus, Nicholas A ^a   Parry, David ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

15 OXO 13 METHOXY 10 AZABENZO[10A,14A]BICYCLO[7.3.1]TRIDECA 3,7 DIYN 5 ENE; 6 ETHOXY 7 HYDROXY 8,11 DIMETHOXYNAPHTHO[2,3 H]QUINOLINE; 8,11 DIMETHOXY 7,12 DIOXO 6 [(TERT BUTYLCARBONYL)OXY]NAPHTHO[2,3 H]QUINOLINE; ANTINEOPLASTIC AGENT; DYNEMICIN A; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; REACTION ANALYSIS;

EID: 0030842824     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970435v     Document Type: Article

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38. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
39. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
40. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
41. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
42. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
43. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
44. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
45. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
46. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
47. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
48. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
49. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
50. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
51. Wood, J. L.; Porco, Jr. J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898. Porco, Jr. J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378. Nicolaou, K. C.; Hwang, C.-K.; Smith, A. L.; Wendeborn, S. V. J. Am. Chem. Soc. 1990, 112, 7416. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890. Nicolaou, K. C.; Hong, Y.-P.; Torisawa. Y.; Tsay, S.-C.; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878. Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908. Dai, W.-M. J. Org. Chem. 1993, 58, 7581. Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755. Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621. Maier, M. E.; Abel, U. Synlett 1994, 38. Wender, P. A.; Beckham, S.; Mohler, D. L. Tetrahedron Lett. 1995, 36, 209. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Beckham, S.; O'Leary, J. O. Synthesis 1994, 1278. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271. Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997. Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449. Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99. Sakamoto, Y.; Takahashi, T. Synlett 1995, 513. Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
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79. 6-propargylic cation reactions and cyclizations, see: Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 3475. Nicholas, K. M.; Nestle, M. O.; Seyferth, D. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749. Montana, A. M.; Nicholas, K. M.; Khan, M. A. J. Org. Chem. 1988, 22, 5193. The symmetrical ether is formulated as i, and is a mixture of diastereomers. (equation presented)
80. 6-propargylic cation reactions and cyclizations, see: Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 3475. Nicholas, K. M.; Nestle, M. O.; Seyferth, D. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749. Montana, A. M.; Nicholas, K. M.; Khan, M. A. J. Org. Chem. 1988, 22, 5193. The symmetrical ether is formulated as i, and is a mixture of diastereomers. (equation presented)
81. 6-propargylic cation reactions and cyclizations, see: Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 3475. Nicholas, K. M.; Nestle, M. O.; Seyferth, D. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. Nicholas, K. M.; Mulraney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Schreiber, S. L.; Klimas, M. Y.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749. Montana, A. M.; Nicholas, K. M.; Khan, M. A. J. Org. Chem. 1988, 22, 5193. The symmetrical ether is formulated as i, and is a mixture of diastereomers. (equation presented)
82. For general discussions of the effects of solvent polarity on reaction rates see: Solvents and Solvent Effects in Organic Chemistry; Reichardt, C., Ed.; VCH: Weinheim, Germany, 1988. Kinetics and Mechanism. A Study of Homogeneous Chemical Reactions; Frost, A. A., Pearson, R. G., Eds.; Wiley: New York, 1963. Mechanism in Organic Chemistry; Alder, R. W., Baker, R., Brown, J. M., Eds.; Wiley: New York, 1975.
83. For general discussions of the effects of solvent polarity on reaction rates see: Solvents and Solvent Effects in Organic Chemistry; Reichardt, C., Ed.; VCH: Weinheim, Germany, 1988. Kinetics and Mechanism. A Study of Homogeneous Chemical Reactions; Frost, A. A., Pearson, R. G., Eds.; Wiley: New York, 1963. Mechanism in Organic Chemistry; Alder, R. W., Baker, R., Brown, J. M., Eds.; Wiley: New York, 1975.
84. For general discussions of the effects of solvent polarity on reaction rates see: Solvents and Solvent Effects in Organic Chemistry; Reichardt, C., Ed.; VCH: Weinheim, Germany, 1988. Kinetics and Mechanism. A Study of Homogeneous Chemical Reactions; Frost, A. A., Pearson, R. G., Eds.; Wiley: New York, 1963. Mechanism in Organic Chemistry; Alder, R. W., Baker, R., Brown, J. M., Eds.; Wiley: New York, 1975.
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89. Weissberg, A.; Taylor, E. C. The Chemistry of Heterocyclic Compounds. Quinoline. Parts I-III; Jones, G., Ed.; Interscience Publications, John Wiley & Sons: London, 1977; Vol. 32. Van der Plas, H. C.; Yamaguchi, T. Recl. Trav. Chim. Pays-Bas. 1977, 96, 89. Cho, I.; Gong, L.; Muchowski, J. M. J. Org. Chem. 1991, 56, 7288. Stanetty, P.; Koller, H.; Mihovilovic, M. J. Org. Chem. 1992, 57, 6833. Arnold, Z. Collect. Czech. Chem. Commun. 1973, 38, 1168. Lloyd, D.; McNab, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 459.
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110. Dr. David Langley (Bristol-Myers Squibb) is thanked for his efforts to match the relative ΔG‡ values by computational methods.
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134. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769. McIntosh, M.; Weinreb, S. J. Org. Chem 1993, 58, 4823.
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136. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
137. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
138. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
139. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
140. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
141. 4,7-Dimethoxyisobenzofuran (iv) was made by treatment of ii with the tetrazine iii. (equation presented) While iv has been reported as an intermediate in various [2 + 4] cycloaddition reactions, it has not been previously isolated presumably because of its assumed instability. For the synthesis of ii see: Cragg, G. M. L.; Giles, R. G. F.; Roos, G. P. H. J. Chem. Soc. Perkin Trans. 1 1975, 1339. iii: Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318. Lynch, V. M.; Fairhurst, R.; Magnus, P.; Davis, B. E. Acta Crystallogr., Sect. C 1995, C51, 780-782. Warrener, R. N. J. Org. Chem. 1971, 93, 2346. Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 13, 4295. Recently Danishefsky has reported the in situ use of 4,7-dimethoxyisobenzofuran for the synthesis of dynemicin analogs; see: Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
142. Brandão, M. A. F.; de Oliveira, A. B.; Snieckus, V. Tetrahedron Lett. 1993, 34, 2437.
143. Snyder, C. D.; Rapoport, H. J. Am. Chem. Soc. 1972, 94, 227.
144. Ho, T.-L.; Hall, T.-W.; Wong, C. M. Synthesis 1973, 206.
145. 6-Acetylene Complexes for the Synthesis of Enediyne Antitumor Antibiotics; SmithKline Beecham Research Symposium, Organometallic Reagents in Organic Synthesis; Academic Press Ltd.: New York, 1994; Chapter 1, p 1. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283.
146. 6-Acetylene Complexes for the Synthesis of Enediyne Antitumor Antibiotics; SmithKline Beecham Research Symposium, Organometallic Reagents in Organic Synthesis; Academic Press Ltd.: New York, 1994; Chapter 1, p 1. Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283.