D,L-Butadiene epoxide

Adler, I.-D., Kliesch, U., Nylund, L. Peltonen, K. (1997) In vitro and in vivo mutagenicity of the butadiene metabolites butadiene diol epoxide, butadiene monoepoxide and diepoxybutane. Mutagenesis, 12, 339-345... 

L-Arcanose and L-olimycose have been prepared in enantiomerically pure forms and with high stereoselectivity by Lewis-acid promoted addition of (5)-2-benzyloxypropanal to 1-tri-methylsilyl-2,3-butadiene. Depending on the nature of the Lewis acid either the syn (with TiCl4) or the anti adduct (with BF3 Et20) can be obtained. Epoxidation with lateral control by the allylic alcohol moieties and standard reactions lead to the unprotected monosaccharides [334]. Total syntheses of 2,3-dideoxy-3-C-methyl-D-maw o-heptose and of 2,3-dideoxy-2,3-di-C-methyl-D-gfycero-D-ga(acto-heptose have been realized by addition of 2-(trimethylsiloxy)furan to 2,3-0-isopropylidene-D-glyceraldehyde ((R)-37) [335]. 

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