Synthesis of enantiopure isoprene epoxides from (s)-lactic acid via 'dispoke' intermediates

Chemical Communications

Volumn , Issue 13, 2000, Pages 1141-1142

  Zhang, Daping ^a   Bleasdale, Christine ^a   Golding, Bernard T ^a   Watson, William P ^b,c  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b SHELL RESEARCH AND TECHNOLOGY CENTRE   (Netherlands)

^c SK10 4TJ   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; ISOPRENE; LACTIC ACID;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034617063     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002133o     Document Type: Article

References (16)

1. National Toxicology Programme TR-486, Toxicology and Carcinogenesis Studies of Isoprene (CAS No. 78-79-5) in F344/N Rats, 1997.
2. G.-J. Boons, R. Downham, K. S. Kim, S. V. Ley and M. Woods, Tetrahedron, 1994, 50, 7157.
3. D. Wistuba, K. Weigand and H. Peter, Chem. Res. Toxicol., 1994, 71, 336; [this paper refers to (S)-2-ethenyl-2-methyloxirane, prepared from (S)-2-methylbut-3-ene-1,2-diol, but gives no information on the source of the latter compound].
4. P. E. Owen and J. R. Glaister, Environ. Health Perspect., 1990, 86, 19.
5. R. L. Melnick and M. C. Kohn, Carcinogenesis, 1995, 16, 157.
6. P. G. Gervasi, L. Citti, M. Del Monte, V. Longo and D. Benetti, Mutat. Res., 1985, 156, 77.
7. J. P. Conkle, B. J. Camp and B. E. Welsch, Arch. Environ. Health, 1975, 30, 290.
8. -1): D. Gelmont, R. D. Stein and J. F. Mead, Biochem. Biophys. Res. Commun., 1981, 99, 1456.
9. T. E. Graedel, D. T. Hawkins and L. D. Claxton, Atmospheric Chemical Compounds. Sources, Occurrence and Bioassay, Academic Press, Orlando, FL, p. 145.
10. F. Loreto and T. D. Sharkey, Plants Cell Environ., 1993, 16, 563.
11. US National Institute for Occupational Safety and Health (1993) National Occupational Exposure Survey (1981-1983), Cincinnati, OH.
12. P. Gervasi and V. Longo, Environ. Health. Perspect., 1990, 86, 85.
13. R. D. Small, B. T. Golding and W. P. Watson, Xenobiotica, 1997, 27, 1155.
14. D. A. Evans, T. C. Britton, J. A. Ellman and R. L. Dorow, J. Am. Chem. Soc., 1990, 112, 4011.
15. M. K. Ellis, B. T. Golding, A. B. Maude and W. P. Watson, J. Chem. Soc., Perkin Trans. 1, 1991, 747.
16. Prepared from rac-2,2-dimethyl-1,3-dioxolane-4-methanol ('solketal') by a sequence of p-methoxybenzylation, acidic hydrolysis and periodate oxidation.