Collect. Czech. Chem. Commun. 1997, 62, 1457-1467
https://doi.org/10.1135/cccc19971457

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

Abstract

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.