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

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.

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 Creators:
Svatoš, Aleš1, Author           
Saman, D., Author
Affiliations:
1External Organizations, ou_persistent22              

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Free keywords: PHEROMONESconjugated dienes; stereoselective synthesis; Peterson-Hudrlik olefination; cuticular hydrocarbons;
 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).

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 Dates: 1997-09
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1135/cccc19971457
Other: EXT288
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Title: Collection of Czechoslovak Chemical Communications
  Other : Collect. Czech. Chem. Commun.
Source Genre: Journal
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Publ. Info: Prague : Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [etc.]
Pages: - Volume / Issue: 62 (9) Sequence Number: - Start / End Page: 1457 - 1467 Identifier: ISSN: 0010-0765
CoNE: https://pure.mpg.de/cone/journals/resource/954925391300