Halonium ion-mediated reaction of unsaturated hydroperoxy acetals. Competition between the formation of cyclic peroxides and the migration of the methoxy (or hydroxy) group

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1069-1075

  Tokuyasu, Takahiro ^a   Masuyama, Araki ^a   Nojima, Masatomo ^a   McCullough, Kevin J ^b  

^a OSAKA UNIVERSITY   (Japan)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; PEROXIDE;

ARTICLE; CELL MIGRATION; COLUMN CHROMATOGRAPHY; COMPETITIVE INHIBITION; CYCLIZATION; DRUG SYNTHESIS; HALOGENATION; REACTION ANALYSIS;

ACETALS; ANTIMALARIALS; CYCLIZATION; DIOXANES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHANOL; MODELS, MOLECULAR; PEROXIDES;

EID: 0034712306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991499m     Document Type: Article

References (39)

1. (a) Jefford, C. W. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsvier: Oxford, 1996; Vol. 6, Chapter 20.
2. (b) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211.
3. (c) Haynes R. K.; Vonwiller, S. C. Acc. Chem. Res. 1997, 30, 73.
4. (d) Robert A.; Meunier, B. Chem. Soc. Rev. 1998, 27, 273.
5. (e) Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmocol. 1997, 37, 253-297.
6. (f) Haynes, R. K.; Pai, H. H.-O.; Voerste, A. Tetrahedron Lett. 1999, 40, 4715.
7. (g) Posner, G. H.; O'Dowd, H.; Caferro, T.; Cumming, J. N.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Tetrahedron Lett. 1998, 39, 2273.
8. (h) Vroman, J. A.; Khan, I. A.; Avery, M. A. Tetrahedron Lett. 1997, 38, 6173.
9. Ushigoe, Y.; Kano, Y.; Nojima, M. J. Chem. Soc., Perkin Trans 1 1997, 5.
10. Dussault, P. H.; Davies, D. R. Tetrahedron Lett. 1996, 37, 463.
11. (a) Meshnick, S. R.; Jefford, C. W.; Posner, G. H.; Avery, M. A.; Peters, W. Parasitol. Today 1996, 12, 79.
12. (b) Boukouvalas, J.; Pouliot, R., Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167.
13. (c) O'Neill, P. M.; Searle, N. L.; Raynes, K. J.; Maggs, J. L.; Ward, S. A.; Storr, R. C.; Park, B. K; Posner, G. H. Tetrahedron Lett. 1998, 39, 6065.
14. (d) Dong, Y.; Matile, H.; Chollet, J.; Kaminsky, R.; Wood, J. K.; Vennerstrom, J. L. J. Med. Chem. 1999, 42, 1477.
15. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
16. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
17. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
18. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
19. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
20. Synthesis of 1,2-dioxanes: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824. (b) Nguyen, V,-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1997, 38, 1773. (c) Fielder, S.; Rowan, D D.; Sherburn, M. S. Tetrahedron 1998, 54, 12907. (d) Bachi, M. D.; Korshin, E. E. Synlett 1998, 122. (e) Jefford, C. W.; Eschenhof, H.; Bernardinelli, G. Heterocycles 1998, 47, 283. (f) Clennan, E. L.; Foote, C. S. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 6.
21. Naturally occurring 1,2-dioxepane: Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaree P.; Clardy, J. Tetrahedron Lett. 1995, 36, 1821. Synthesis of 1,2-dioxepanes: (a) Ninomiya, I.; Naito, T.; Miyata, O. In Comprehesive Heterocyclic Chemistry II; Newkome, G. R., Ed.; Elsevier: Oxford, 1996; Vol. 9, pp 233-238 and 1039-1146. (b) Kajikawa, S.; Noiri, Y.; Shudo, H.; Nishino, H.; Kurosawa, K. Synthesis 1998, 1457. (c) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784. Haraldson, C. A.; Karle, J. M.; Freeman, S. G.; Duvadie, R. K.; Avery, M. A. Bioorg. Med. Chem. Lett. 1997, 7, 2357.
22. Naturally occurring 1,2-dioxepane: Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaree P.; Clardy, J. Tetrahedron Lett. 1995, 36, 1821. Synthesis of 1,2-dioxepanes: (a) Ninomiya, I.; Naito, T.; Miyata, O. In Comprehesive Heterocyclic Chemistry II; Newkome, G. R., Ed.; Elsevier: Oxford, 1996; Vol. 9, pp 233-238 and 1039-1146. (b) Kajikawa, S.; Noiri, Y.; Shudo, H.; Nishino, H.; Kurosawa, K. Synthesis 1998, 1457. (c) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784. Haraldson, C. A.; Karle, J. M.; Freeman, S. G.; Duvadie, R. K.; Avery, M. A. Bioorg. Med. Chem. Lett. 1997, 7, 2357.
23. Naturally occurring 1,2-dioxepane: Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaree P.; Clardy, J. Tetrahedron Lett. 1995, 36, 1821. Synthesis of 1,2-dioxepanes: (a) Ninomiya, I.; Naito, T.; Miyata, O. In Comprehesive Heterocyclic Chemistry II; Newkome, G. R., Ed.; Elsevier: Oxford, 1996; Vol. 9, pp 233-238 and 1039-1146. (b) Kajikawa, S.; Noiri, Y.; Shudo, H.; Nishino, H.; Kurosawa, K. Synthesis 1998, 1457. (c) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784. Haraldson, C. A.; Karle, J. M.; Freeman, S. G.; Duvadie, R. K.; Avery, M. A. Bioorg. Med. Chem. Lett. 1997, 7, 2357.
24. Naturally occurring 1,2-dioxepane: Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaree P.; Clardy, J. Tetrahedron Lett. 1995, 36, 1821. Synthesis of 1,2-dioxepanes: (a) Ninomiya, I.; Naito, T.; Miyata, O. In Comprehesive Heterocyclic Chemistry II; Newkome, G. R., Ed.; Elsevier: Oxford, 1996; Vol. 9, pp 233-238 and 1039-1146. (b) Kajikawa, S.; Noiri, Y.; Shudo, H.; Nishino, H.; Kurosawa, K. Synthesis 1998, 1457. (c) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784. Haraldson, C. A.; Karle, J. M.; Freeman, S. G.; Duvadie, R. K.; Avery, M. A. Bioorg. Med. Chem. Lett. 1997, 7, 2357.
25. Naturally occurring 1,2-dioxepane: Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaree P.; Clardy, J. Tetrahedron Lett. 1995, 36, 1821. Synthesis of 1,2-dioxepanes: (a) Ninomiya, I.; Naito, T.; Miyata, O. In Comprehesive Heterocyclic Chemistry II; Newkome, G. R., Ed.; Elsevier: Oxford, 1996; Vol. 9, pp 233-238 and 1039-1146. (b) Kajikawa, S.; Noiri, Y.; Shudo, H.; Nishino, H.; Kurosawa, K. Synthesis 1998, 1457. (c) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784. Haraldson, C. A.; Karle, J. M.; Freeman, S. G.; Duvadie, R. K.; Avery, M. A. Bioorg. Med. Chem. Lett. 1997, 7, 2357.
26. The related singlet oxygenation of 1-methoxymethylene-2-(2-cycanoethyl)cyclohexane also shows the same diastereoselectivity: (a) Hamzaoui, M.; Provot, O.; Camuzat-Dedenis, B.; Moskowitz, H.; Mayrargue, J.; Ciceron, L.; Gay, F. Tetrahedron Lett. 1998, 39, 4029. (b) Cumming, J. N.; Wang, D.; Park, S. B.; Shapiro, T. A.; Posner, G. H. J. Med. Chem. 1998, 41, 952.
27. The related singlet oxygenation of 1-methoxymethylene-2-(2- cycanoethyl)cyclohexane also shows the same diastereoselectivity: (a) Hamzaoui, M.; Provot, O.; Camuzat-Dedenis, B.; Moskowitz, H.; Mayrargue, J.; Ciceron, L.; Gay, F. Tetrahedron Lett. 1998, 39, 4029. (b) Cumming, J. N.; Wang, D.; Park, S. B.; Shapiro, T. A.; Posner, G. H. J. Med. Chem. 1998, 41, 952.
28. Dussault, P. H.; Zope, U. R. J. Org. Chem. 1995, 60, 8218.
29. For a general discussion for the halonium ion-mediated cylization see: (a) Rousseau, G.; Homsi, F. Chem. Soc. Rev. 1997, 26, 453. (b) Kitagawa, O.; Taguchi, T. J. Synth. Org. Chem. Jpn. 1998, 56, 661.
30. For a general discussion for the halonium ion-mediated cylization see: (a) Rousseau, G.; Homsi, F. Chem. Soc. Rev. 1997, 26, 453. (b) Kitagawa, O.; Taguchi, T. J. Synth. Org. Chem. Jpn. 1998, 56, 661.
31. Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 1.9.
32. w = 0.084. The X-ray diffraction data were collected on a Siemens P4 diffractometer using graphite-monochromated Mo Kα (λ = 0.710 73 Å) at T = 160 K and corrected for absorption, and the structure was solved by direct methods. All crystallographic calculations were carried out using SHELXTL (version 5.1) (Sheldrick, G. M., Brucker AXS Inc., Madison, WI).
33. A similar C-O bond formation with the concomitant O-O bond fission has been proposed for the formation of 2-bromo-9-oxabicyclo-[4.2.1]nonane from the reaction of 5-hydroperoxycyclooctene with NBS: Bloodworth, A. J.; Curtis, R. J.; Spencer, M. D.; Tallant, N. A. Tetrahedron 1993, 49, 2729.
34. Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1337.
35. Fukagawa, R.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1994, 2449.
36. (a) Lutz, R. E. Love, L. Jr.; Palmer, F. S. J. Am. Chem. Soc. 1935, 57, 1953.
37. (b) Marvel, C. S.; Gall, E. J. J. Org. Chem. 1960, 25, 1784.
38. Simonot, B.; Rousseau, G. J. Org. Chem. 1994, 59, 5912.
39. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.