Endo mode cyclization of 5,6-epoxy-7-octyn-1-ol derivatives

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6761-6765

  Mukai, Chisato ^a   Yamaguchi, Sumie ^a   Sugimoto, Yu Ichi ^a   Miyakoshi, Naoki ^a   Kasamatsu, Eiji ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5,6 EPOXY 7 OCTYN 1 OL DERIVATIVE; EPOXIDE; OXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034613289     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000450+     Document Type: Article

References (27)

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13. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
14. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
15. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
16. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
17. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
18. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
19. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
20. Review for synthesis of of seven-membered oxacycles: (a) Boyd, D. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 547. (b) Hassenruck, K.; Martin H. D. Synthesis 1988, 569. (c) Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, p 201. (d) Burns, C. J. Contemp. Org. Synth. 1994, 1, 23. (e) Wlliott, M. C. Contemp. Org. Synth. 1994, 1, 457. (f) Alvarez, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953. (g) Belen'kll, L. I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: Oxford, 1996; p 45. (h) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589. (i) Hoberg, J. O. Tetrahedron 1998, 54, 12631, and references therein.
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27. Spectral data of 12 and 13 are presented in Supporting Information.