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

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Title:Efficient Stereoselective Synthesis of All Geometrical Isomers of Heptadeca-11,13-dienes
Creators:
Svatoš, Aleš
Šaman, David
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 9, pp. 1457-1467
Uncontrolled Keywords:Cuticular hydrocarbons, Stereoselective synthesis, Peterson-Hudrlik olefination, Conjugated dienes

Abstract

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

Title:Efficient Stereoselective Synthesis of All Geometrical Isomers of Heptadeca-11,13-dienes
Creators:
Svatoš, Aleš
Šaman, David
Uncontrolled Keywords:Cuticular hydrocarbons, Stereoselective synthesis, Peterson-Hudrlik olefination, Conjugated dienes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:9
Page Range:pp. 1457-1467
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971457UNSPECIFIED
ID Code:1221
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Svatoš, Aleš; Šaman, David (1997) Efficient Stereoselective Synthesis of All Geometrical Isomers of Heptadeca-11,13-dienes. Collection of Czechoslovak Chemical Communications, 62 (9). pp. 1457-1467. ISSN 0010-0765

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