Total synthesis of (±)-FR66979

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4688-4691

  Ducray, Richard ^a,b   Ciufolini, Marco A ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b Electron de Lyon   (France)

Author keywords

Antitumor agents; Asymmetric synthesis; Natural products; Rearrangement; Total synthesis

Indexed keywords

SYNTHESIS (CHEMICAL); TUMORS;

ANTITUMOR AGENTS; TRANSPOSITION;

BIOCHEMISTRY;

ANTINEOPLASTIC AGENT; AZIRIDINE; FR 66979; UNCLASSIFIED DRUG; OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; DRUG SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ISOMERISM; MOLECULAR STRUCTURE; OXAZINES;

EID: 0037121441     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290017     Document Type: Article

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31. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
32. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
33. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
34. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
35. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
36. For total syntheses of 1 b, see: a) T. Fukuyama, L. Xu, S. Goto, J. Am. Chem. Soc. 1992, 114, 383; b) J. M. Schkeryantz, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 4722; c) T. Katoh, E. Itoh, T. Yoshino, S. Terashima, Tetrahedron 1997, 53, 10229; d) T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239; e) T. Katoh, Y. Nagata, T. Yoshino, S. Nakatani, S. Terashima, Tetrahedron 1997, 53, 10253; see also two previous communications: f) T. C. Judd, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; g) M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.We are grateful to Profs. Robert M. Williams and Tohru Fukuyama for informing us of their independent syntheses of FR-900482 and FR-66979 prior to submission of our work, and for agreeing to have our three papers appear consecutively in this issue of Angewandte Chemie.
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