Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 649-652

  Carless, Howard A J ^a   Dove, Yvonne ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXYSHIKIMIC ACID; CYCLOHEXENE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029869280     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00055-9     Document Type: Article

References (34)

1. Balci, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron, 1990, 46, 3715: Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives, VCH, New York, 1993.
2. Balci, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron, 1990, 46, 3715: Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives, VCH, New York, 1993.
3. Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem., 1990, 48, 21; Suami, T. Top. Curr: Chem., 1990, 154, 251.
4. Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem., 1990, 48, 21; Suami, T. Top. Curr: Chem., 1990, 154, 251.
5. Reviews: Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta. 1990, 8 (No. 3), 3; Carless. H. A. J. Tetrahedron: Asymmetry, 1992, 3, 795; Sheldrake, G. N. in Chirality in Industry, ed. Collins, A. N.; Sheldrake, G. N.; Crosby, J.; Wiley, Chichester, 1992, 127; Brown, S. M.; Hudlicky, T.; in Organic Synthesis: Theory and Applications, ed. Hudlicky, T.; JAI Press, Greenwich, Connecticut, 1993, vol.2, 113.
6. Reviews: Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta. 1990, 8 (No. 3), 3; Carless. H. A. J. Tetrahedron: Asymmetry, 1992, 3, 795; Sheldrake, G. N. in Chirality in Industry, ed. Collins, A. N.; Sheldrake, G. N.; Crosby, J.; Wiley, Chichester, 1992, 127; Brown, S. M.; Hudlicky, T.; in Organic Synthesis: Theory and Applications, ed. Hudlicky, T.; JAI Press, Greenwich, Connecticut, 1993, vol.2, 113.
7. Reviews: Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta. 1990, 8 (No. 3), 3; Carless. H. A. J. Tetrahedron: Asymmetry, 1992, 3, 795; Sheldrake, G. N. in Chirality in Industry, ed. Collins, A. N.; Sheldrake, G. N.; Crosby, J.; Wiley, Chichester, 1992, 127; Brown, S. M.; Hudlicky, T.; in Organic Synthesis: Theory and Applications, ed. Hudlicky, T.; JAI Press, Greenwich, Connecticut, 1993, vol.2, 113.
8. Reviews: Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta. 1990, 8 (No. 3), 3; Carless. H. A. J. Tetrahedron: Asymmetry, 1992, 3, 795; Sheldrake, G. N. in Chirality in Industry, ed. Collins, A. N.; Sheldrake, G. N.; Crosby, J.; Wiley, Chichester, 1992, 127; Brown, S. M.; Hudlicky, T.; in Organic Synthesis: Theory and Applications, ed. Hudlicky, T.; JAI Press, Greenwich, Connecticut, 1993, vol.2, 113.
9. For recent synthetic applications, and in cyclitol synthesis, see Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.; Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147; Hudlicky, T.; Thorpe, A. J. Synlett, 1994, 899; Roberts, S. M.; Sutton, P. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1499; Jenkins, G. N.; Ribbons, D. W.; Widdowson, D. A.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1, 1995, 2647; for an alternative approach to cyclitols from arenes, see Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl. 1995, 14, 2031.
10. For recent synthetic applications, and in cyclitol synthesis, see Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.; Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147; Hudlicky, T.; Thorpe, A. J. Synlett, 1994, 899; Roberts, S. M.; Sutton, P. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1499; Jenkins, G. N.; Ribbons, D. W.; Widdowson, D. A.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1, 1995, 2647; for an alternative approach to cyclitols from arenes, see Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl. 1995, 14, 2031.
11. For recent synthetic applications, and in cyclitol synthesis, see Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.; Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147; Hudlicky, T.; Thorpe, A. J. Synlett, 1994, 899; Roberts, S. M.; Sutton, P. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1499; Jenkins, G. N.; Ribbons, D. W.; Widdowson, D. A.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1, 1995, 2647; for an alternative approach to cyclitols from arenes, see Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl. 1995, 14, 2031.
12. For recent synthetic applications, and in cyclitol synthesis, see Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.; Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147; Hudlicky, T.; Thorpe, A. J. Synlett, 1994, 899; Roberts, S. M.; Sutton, P. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1499; Jenkins, G. N.; Ribbons, D. W.; Widdowson, D. A.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1, 1995, 2647; for an alternative approach to cyclitols from arenes, see Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl. 1995, 14, 2031.
13. For recent synthetic applications, and in cyclitol synthesis, see Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Dalton, H.; Chima, J.; Whited, G.; Seemayer, R. J. Am. Chem. Soc., 1994, 116, 1147; Hudlicky, T.; Thorpe, A. J. Synlett, 1994, 899; Roberts, S. M.; Sutton, P. W. J. Chem. Soc., Perkin Trans. 1, 1995, 1499; Jenkins, G. N.; Ribbons, D. W.; Widdowson, D. A.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1, 1995, 2647; for an alternative approach to cyclitols from arenes, see Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl. 1995, 14, 2031.
14. Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron Lett., 1995, 36, 6545; earlier resolutions of intermediates derived from 2: Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun., 1991, 1006: Ley, S.V.; Yeung, L. L. Synlett. 1992, 997.
15. Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron Lett., 1995, 36, 6545; earlier resolutions of intermediates derived from 2: Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun., 1991, 1006: Ley, S.V.; Yeung, L. L. Synlett. 1992, 997.
16. Nicolosi, G.; Patti, A.; Piattelli, M.; Sanfilippo, C. Tetrahedron Lett., 1995, 36, 6545; earlier resolutions of intermediates derived from 2: Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun., 1991, 1006: Ley, S.V.; Yeung, L. L. Synlett. 1992, 997.
17. Johnson, C. R.; Adams, J. P.; Collins, M. A. J. Chem. Soc., Perkin Trans, 1. 1993, 1.
18. Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett, 1992, 245.
19. Entwistle, D. A.; Hudlicky, T. Tetrahedron Lett., 1995, 36, 2591.
20. Carless, H. A. J.; Malik, S. S. J. Chem. Soc., Chem. Commun., 1995, 2447.
21. Review: Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis. 1993, 179.
22. Recent examples: Wood, H. B., Jr.; Ganem, B. Tetrahedron Lett., 1993, 34, 1403: Jiang, S.; Mekki, B.; Singh, G.; Wightman, R. H.; Tetrahedron Lett., 1994, 35, 5505; Meier, R. M.; Ganem. B. J. Org. Chem., 1994, 59, 5436.
23. Recent examples: Wood, H. B., Jr.; Ganem, B. Tetrahedron Lett., 1993, 34, 1403: Jiang, S.; Mekki, B.; Singh, G.; Wightman, R. H.; Tetrahedron Lett., 1994, 35, 5505; Meier, R. M.; Ganem. B. J. Org. Chem., 1994, 59, 5436.
24. Recent examples: Wood, H. B., Jr.; Ganem, B. Tetrahedron Lett., 1993, 34, 1403: Jiang, S.; Mekki, B.; Singh, G.; Wightman, R. H.; Tetrahedron Lett., 1994, 35, 5505; Meier, R. M.; Ganem. B. J. Org. Chem., 1994, 59, 5436.
25. Synthesis: (a) Sutherland, J. K.; Watkins, W. J.; Bailey, J. P.; Chapman, A. K.; Davies, G. M. J. Chem. Soc., Chem. Commun., 1989, 1386;
26. (b) Sutherland, J. K.; Whitehead, R. C.; Davies, G. M. J. Chem. Soc., Chem. Commun., 1993, 464;
27. (c) Bowles, S. A.; Campbell, M. M.; Sainsbury, M.; Davies, G. M. Tetrahedron, 1990, 46, 3981; Activity:
28. (d) Ewart, C. D. C.; Jude, D. A.; Thain, J. L.; Nichols, W. W. Antimicrob. Agents Chemotherapy, 1995, 39, 87;
29. (e) Davies, G. M.; Barrettbee, K. J.; Jude, D. A.; Lehan, M.; Nichols, W. W.; Pinder, P. E.; Thain, J. L.; Watkins, W. J.; Wilson, R. G. Antimicrob. Agents Chemotherapy, 1994, 38, 403.
30. Benzonitrile cis-dihydrodiol, 3-cyanocyclohexa-3,5-diene-1,2-diol, has (1S,2R) configuration: Boyd, D. R.; Hand, M. V.; Sharma, N. D.; Chima, J.; Dalton, H.; Sheldrake, G. N. J. Chem. Soc., Chem. Commun., 1991, 1630; it is commercially available (product GC 904) from Genencor International Inc., Rochester. NY, 14618, USA.
31. 3. Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Sik, V.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1, 1989, 1160: X = C1, Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc., 1994, 116, 5108 and references therein.
32. 3. Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Sik, V.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1, 1989, 1160: X = C1, Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc., 1994, 116, 5108 and references therein.
33. See reference 12(b) for a previous multi-step route to 20 from quinic acid.
34. Bal, S. B.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron, 1981, 37, 2091.