| Abstrakt: |
Methyl cis-9, cis-12, cis-15-octadecatrienoate-15,16- d was obtained from Wittig coupling of methyl 12-oxo- cis-9-dodecenoate, 18, and 3,4-dideutero- cis-3-hexenyltriphenylphosphonium bromide, 16. Compound 18 was obtained by periodic acid oxidation of methyl 12,13-dihydroxy- cis-9-octadecenoate, 17, obtained from Vernonia oil. Compound 18 also was synthesized from methyl oleate as the starting material. The deuterated fragment, 16, was prepared from 3-hexynol and using Lindlar's catalyst and deuterium gas to introduce the deuterium atoms. Methyl cis-9, cis-12, cis-15-octadecatrienoate-6,6,7,7- d was prepared by Wittig coupling of 3,6-nonadienyltriphenylphosphonium iodide, 5, with methyl 9-oxononanoate-6,6,7,7- d , 11. Deuterium atoms were introduced during the synthesis of 11 from 3-butynol and 5-bromopentanoic acid with deuterium gas in the presence of [PhP]-RhCl. For the preparation of 5, the 3,6-nonadiynol intermediate was reduced to 3,6-nonadienol with P-2 Nickel and hydrogen. The final products were separated from isomers formed during the synthetic sequences by silver resin chromatography. [ABSTRACT FROM AUTHOR] |
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