Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide

Synthetic Communications

Volumn 32, Issue 19, 2002, Pages 3041-3045

  Claffey, David J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

Butadiene; Mesobutadiene bisepoxide; Metabolite; Synthesis

Indexed keywords

1,3 BUTADIENE DERIVATIVE; CARCINOGEN; MESO 1,3 BUTADIENE BISEPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HUMAN; METABOLITE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TOXICOKINETICS;

EID: 0036383950     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120012996     Document Type: Article

References (12)

1. Hanesian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: Oxford, 1983.
2. Henderson, R.F.; Barr, E.B.; Belinsky, S.A.; Benson, J.M.; Hahn, F.F.; Menache, M.G. 1,3-Butadiene: Cancer, Mutations, and Adducts. Part I: Carcinogenicity of 1,2,3,4-diepoxybutane. Research Report-H.E.I. 2000, 92(11-43), 45-48.
3. Saranko, C.J.; Meyer, K.G.; Pluta, L.J.; Henderson, R.F.; Recio, L. Lung-Specific Mutagenicity and Mutational Spectrum in B6C3F1 1acI Transgenic Mice Following Inhalation Exposure to 1,2-Epoxybutene. Mutat. Res. 2001, 473(1), 37-49.
4. IARC. Occupational Exposures to Mists and Vapors from Strong Inorganic Acids and Other Industrial Chemicals, 1,3-Butadiene. IARC Monogr. 1992, 54, 237-287.
5. Neagu, C.; Tapio, H. Synthesis of Enantiomerically Pure 3-Butene-1,2-Diol Derivatives via a Sharpless Asymmetric Epoxidation Route. Tetrahedron Lett. 1993, 34(10), 1629-1630.
6. Nieusma, J.L.; Claffey, D.J.; Ruth, J.A.; Ross, D. Stereochemical Aspects of the Conjugation of Epoxide Metabolites of Butadiene with Glutathione in Rat Liver Cytosol and Freshly Isolated Rat Hepatocytes. Tox. Sci. 1998, 43, 102-109.
7. Irons, R.D.; Pyatt, D.W.; Stillman, W.S.; Som, D.B.; Claffey, D.J.; Ruth, J.A. Comparative Toxicity of Known and Putative Metabolites of 1,3-Butadiene in Human CD34+ Bone Marrow Cells. Toxicology 2000, 150, 99-106.
8. Monnier, J.R. The Selective Epoxidation of Non-Allylic Olefins Over Supported Silver Catalysts. 3rd World Congress on Oxidation Catalysis: Studies in Surface Science and Catalysis. 1997, 110, 135-149.
9. Melnik, L.V.; Nozhnin, N.A.; Grechina, N.V.; Kryukov, S.I.; Yegorova, L.M.; Danilova, A.S. Synthesis of 1,2,3,4-diepoxybutane from 1,3-Butadiene Monoxide. Petroleum Chem. 1996, 36(5), 455-459.
10. Stojanowa-Antoszczyszyn, M.; Myszkowski, J.; Wisnik, I.; Gawronska, A. Synthesis of Diepoxybutane from Dichloro-butanediols. Przem. Chem. 1977, 56(5), 246-250. Chem. Abs. 88:6620r.
11. Kabalka, G.W.; Varma, M.; Varma, R.S. Tosylation of Alcohols. J. Org. Chem. 1986, 51, 2386-2388.
12. Larock, R.C. Comprehensive Organic Transformations, 2nd Ed.; Wiley-VCH: New York, 1999.