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Efficient stereoselective synthesis of all geometrical isomers of heptadeca-11,13-dienes

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Svatoš, A., & Saman, D. (1997). Efficient stereoselective synthesis of all geometrical isomers of heptadeca-11,13-dienes. Collection of Czechoslovak Chemical Communications, 62(9), 1457-1467. doi:10.1135/cccc19971457.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0015-0F3A-2
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-beta-hydroxysilanes (15 and 17). These (Z)- and (E)-alkenyl-beta-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% (C-13 NMR).