Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 14, 1996, Pages 1757-1765

  Boyd, Derek R ^a   Sharma, Narain D ^a   Boyle, Rosemary ^a   Evans, Timothy A ^a   Malone, John F ^a   McCombe, Kenneth M ^a   Dalton, Howard ^b   Chima, Jagdeep ^b  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748890274     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001757     Document Type: Article

References (29)

1. E. E. Schweizer and D. Meeder-Nycz, in Chromenes, Chromanones, and Chromones, ed. G. P. Ellis, The Chemistry of Heterocyclic Compounds, Wiley and Sons, New York, 1977, 29.
2. T. R. Kasturi and T. Manithomas, Tetrahedron Lett., 1967, 2573.
3. G. B. Staal, Ann. Rev. Entomol., 1986, 31, 391.
4. R. A. Halpin, K. P. Vyas, S. F. El-Nagger and D. M. Jerina, Chem. Biol. Interact., 1984, 48, 297.
5. R. A. Halpin, S. F. El-Naggar, K. M. McCombe, K. P. Vyas, D. R. Boyd and D. M. Jerina, Tetrahedron Lett., 1982, 23, 1655.
6. R. C. Jennings and A. P. Ottridge, J. Chem. Soc., Perkin Trans. 1, 1984, 1733.
7. A. Conchillo, F. Camps and A. Messeguer, J. Org. Chem., 1990, 55, 1728.
8. J. Bujous, F. Camps and A. Messeguer, Tetrahedron Lett., 1990, 31, 5235.
9. J. M. Evans and G. Stemp, Chem. Br., 1991, 439.
10. D. R. Boyd, N. D. Sharma, R. Boyle, B. T. McMurray, T. A. Evans, J. F. Malone, H. Dalton, J. Chima and G. N. Sheldrake, J. Chem. Soc., Chem. Commun., 1993, 49.
11. D. R. Boyd, R. A. S. McMordie, N. D. Sharma, H. Dalton, P. Williams and R. O. Jenkins, J. Chem. Soc., Chem. Commun., 1989, 339.
12. D. R. Boyd, N. D. Sharma, N. A. Kerley, R. A. S. McMordie, G. N. Sheldrake, P. Williams and H. Dalton, J. Chem. Soc., Perkin Trans. 1, 1996, 67.
13. G. E. Stokker, J. Heterocycl. Chem., 1984, 21, 609.
14. B. B. Lohray, Tetrahedron: Asymmetry, 1992, 3, 1317.
15. Z.-M. Wang, K. Kakiuchi and K. B. Sharpless, J. Org. Chem., 1994, 59, 6895.
16. S. Hanessian, P. Meffre, M. Girard, S. Beaudoin, J.-V. Sanceau and Y. Bennani, J. Org. Chem., 1993, 115, 8463.
17. S. K. Balani, D. R. Boyd, S. E. Cassidy, G. I. Devine, J. F. Malone, K. M. McCombe, N. D. Sharma and W. B. Jennings, J. Chem. Soc., Perkin Trans. 1, 1983, 2751.
18. S. N. Vander Velder and E. N. Jacobsen, J. Org. Chem., 1995, 60, 5381.
19. W. E. Parham and L. D. Huestis, J. Am. Chem. Soc., 1962, 84, 813.
20. L. I. Smith and P. M. Ruoff, J. Am. Chem. Soc., 1940, 62, 145.
21. D. R. Boyd, M. R. J. Dorrity, J. F. Malone, R. A. S. McMordie, N. D. Sharma, H. Dalton and P. Williams, J. Chem. Soc., Perkin Trans. 1, 1990, 489.
22. J. Buckingham, in Dictionary of Organic Compounds, Chapman and Hall, New York, 1982, 1, 573.
23. J. H. Billman and J. A. Tomis, J. Pharm. Sci., 1971, 60, 1118.
24. F. Baranton, G. Fontaine and P. Maitte, C. R. Acad. Sci. Paris Ser. C, 1967, 264, 410.
25. W. D. Cotterill, J. Cottam and R. Livingstone, J. Chem. Soc. C, 1970, 1006.
26. H. L. Holland, T. S. Manoharan and F. Schweizer, Tetrahedron: Asymmetry, 1991, 2, 335.
27. G. M. Sheldrick, SHELXS-86, Program for crystal structure solution, Acta Crystal., Sect. A, 1990, 46, 467.
28. G. M. Sheldrick, SHELXL-93, Program for crystal structure refinement, University of Göttingen, 1993.
29. R. Livingstone, J. Chem. Soc., 1962, 76.