Three-Component Homo 3 + 2 Dipolar Cycloaddition. A Diversity-Oriented Synthesis of Tetrahydro-1,2-oxazines and FR900482 Skeletal Congeners

Organic Letters

Volumn 6, Issue 1, 2004, Pages 139-141

  Young, Ian S ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ALDEHYDE; CYCLOPROPANE DERIVATIVE; HYDROXYLAMINE; NITRONE DERIVATIVE; OXAZINE DERIVATIVE;

ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0742304177     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0362919     Document Type: Article

References (19)

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4. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
5. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
6. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
7. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
8. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
9. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
10. Racemic total syntheses: (a) Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383-385. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723. Enantioselective total syntheses: (c) Kato, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10253-10270. (d) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683-4685. (e) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686-4688. (f) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130-138. For a synthesis of related racemic FR66979, see: (g) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2002, 41, 4688-4691.
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