An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

Synthesis

Volumn , Issue 10, 2003, Pages 1500-1502

  Baran, Arif ^a   Seçen, Hasan ^a   Balci, Metin ^b  

^a ATATÜRK UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Alcohols; Cyclitol; Cyclohexol; Eliminations; Hydroxylation; Quercitol; Stereoselective synthesis

Indexed keywords

ACETYLATION; HYDROLYSIS; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DEMETHYLATION;

AROMATIC HYDROCARBONS;

1,3 DIOXOLANE DERIVATIVE; 1,4 CYCLOHEXADIENE; 5 METHOXY 2,2 DIMETHYL 3A,4,5,7A TETRAHYDRO 1,3 BENZODIOXOLE; 5 O METHYL GALAQUERCITOL TETRAACETATE; 5,6 DIBROMO 2,2 DIMETHYLHEXAHYDRO 1,3 BENZODIOXOLE; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALKADIENE; GALAQUERCITOL; HYDROBROMIC ACID; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL REACTION; DEMETHYLATION; HYDROLYSIS; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0041743702     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40517     Document Type: Article

References (33)

1. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
2. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
3. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
4. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
5. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
6. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
7. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
8. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
9. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
10. For recent cyclitol synthesis see: (a) Yadav, J. S.; Maiti, A.; Sankar, A. R.; Kunwar, A. C. J. Org. Chem. 2001, 66, 8370. (b) Ogawa, S.; Aoyama, H.; Tezuka, Y. J. Carbohyd. Chem. 2001, 20, 703. (c) Mehta, G.; Ramesh, S. S. Chem. Commun. 2000, 2429. (d) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2000, 41, 3509. (e) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (f) Desjardins, M.; Lallemand, M. C.; Freeman, S.; Hudlicky, T.; Abboud, K. A. J. Chem. Soc. Perkin., Trans. J 1999, 1, 621. (g) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219. (h) Lee, W. W.; Chang, S. Tetrahedron: Asymmetry 1999, 10, 4473. (i) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10834. (j) Yoshizaki, H.; Backvall, J. E. J. Org. Chem. 1998, 63, 9339.
11. Sütbeyaz, Y.; Seçen, H.; Balci, M. J. Chem. Soc., Chem. Commun. 1988, 1330.
12. Seçen, H.; Sütbeyaz, Y.; Balci, M. Tetrahedron Lett. 1990, 31, 1323.
13. (a) Seçen, H.; Salamci, E.; Sütbeyaz, Y.; Balci, M. Synlett 1993, 609.
14. (b) Salamci, E.; Seçen, H.; Sütbeyaz, Y.; Balci, M. Synth. Commun. 1997, 27, 2223.
15. (c) Salamci, E.; Seçen, H.; Sütbeyaz, Y.; Balci, M. J. Org. Chem. 1997, 62, 2453.
16. (d) Balci, M. Pure Appl. Chem. 1997, 69, 97.
17. Mara, A.; Seçen, H.; Sütbeyaz, Y.; Balci, M. J. Org. Chem. 1998, 63, 2039.
18. Mara, A.; Erden, M.; Seçen, H.; Sütbeyaz, Y. Carbohydr. Res. 1998, 308, 435.
19. Seçen, H.; Gültekin, M. S.; Sütbeyaz, Y.; Balci, M. Turk. J. Chem. 1993, 17, 108.
20. Akbulut, N.; Balci, M. J. Org. Chem. 1988, 53, 3338.
21. For the synthesis of protected versions of 1 and 2 see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Haines, A. H.; King, A. S. H.; Knight, J. R.; Nguyen, V.-A. Tetrahedron Lett. 1998, 39, 4393. (c) Kim, K. S.; Park, J. I.; Moon, H. K.; Yi, H. Chem. Commun. 1998, 1945.
22. For the synthesis of protected versions of 1 and 2 see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Haines, A. H.; King, A. S. H.; Knight, J. R.; Nguyen, V.-A. Tetrahedron Lett. 1998, 39, 4393. (c) Kim, K. S.; Park, J. I.; Moon, H. K.; Yi, H. Chem. Commun. 1998, 1945.
23. For the synthesis of protected versions of 1 and 2 see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Haines, A. H.; King, A. S. H.; Knight, J. R.; Nguyen, V.-A. Tetrahedron Lett. 1998, 39, 4393. (c) Kim, K. S.; Park, J. I.; Moon, H. K.; Yi, H. Chem. Commun. 1998, 1945.
24. (a) Nakajima, M.; Kurihara, N. Chem. Ber. 1961, 94, 515.
25. (b) McCasland, G. E. Adv. Carbohydr. Chem. 1965, 20, 11.
26. McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335.
27. Angyal, S. J.; Odier, L. Carbohydr. Res. 1981, 101, 209.
28. Angelaud, R.; Landais, Y. J. Org. Chem. 1996, 61, 5202.
29. Dubreuil, D.; Cleophax, J.; Almeida, M. V.; Verre-Sebrie, C.; Liaigre, J.; Vass, G.; Gero, S. D. Tetrahedron 1997, 53, 16747.
30. Maezaki, N.; Nagahashi, N.; Yoshigami, R.; Iwata, C.; Tanaka, T. Tetrahedron Lett. 1999, 40, 3781.
31. Yang, N. C.; Chen, M. J.; Chen, P. J. Am. Chem. Soc. 1984, 106, 7310.
32. Gogek, C. J.; Moir, R. Y.; McRae, J. A.; Purves, C. B. Can. J. Chem. 1951, 29, 938.
33. Wibaut, J. P.; Hauk, F. A. Recl. Trav. Chim. Pays-Bas 1948, 67, 91.