Collect. Czech. Chem. Commun. 1997, 62, 1457-1467

Efficient Stereoselective Synthesis of All Geometrical Isomers of Heptadeca-11,13-dienes

Aleš Svatoš and David Šaman

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


All geometrical isomers of heptacosa-11,13-dienes, 1-4, previously identified in termite Prorhinotermes simplex cuticular hydrocarbons, were efficiently synthesized according Peterson-Hudrlik olefination procedure in high stereoisomeric purity using syn and anti elimination of erythro alkenyl-β-hydroxysilanes (15 and 17). These (Z)- and (E)-alkenyl-β-hydroxysilanes are available from regioselective opening of (1R*,2S*)-1,2-epoxy-1-trimethylsilylpentadecane 13 with corresponding (Z)- and (E)-dodec-1-enyl cuprates (14 and 16). Stereoisomeric purity of obtained dienes 1-4 was higher than 95% (13C NMR).

Keywords: Conjugated dienes; Stereoselective synthesis; Peterson-Hudrlik olefination; Cuticular hydrocarbons.