133707-14-9Relevant articles and documents
ON THE COHERENCE OF INCORPORATION OF THE FLUOROVINYL MOIETY INTO BIOACTIVE ORGANIC COMPOUNDS. SYNTHESIS OF AN INSECT JUVENILE HORMONE III FLUORINATED ANALOG.
Camps, F.,Messeguer, A.,Sanchez, Francisco-Jose
, p. 5161 - 5168 (1988)
An insect juvenile hormone fluoroanalog, methyl 10-fluoro-10,11-epoxyfarnesoate (9), has been prepared, using tandem Claisen-Cope rearrangements on fluorovinyl intermediate 1 as a crucial step.Along this synthesis chemical and spectral data have been obtained that might question some applications of fluorovinyl derivatives in the design of bioactive organic compounds.
Epoxidation of Carbon-Carbon Double Bonds in Terpenes by Linoleic Acid Hydroperoxides
Meyer, Werner,Spiteller, Gerhard
, p. 1253 - 1256 (2007/10/02)
Epoxidation of C=C double bonds in terpenes is achieved by reaction with linoleic acid hydroperoxides (LOOH) exemplified with caryophyllene (3), methyl farnesoate (5) and squalene (8).Linoleic acid (9S)-hydroperoxide was obtained by reaction of linoleic acid (1) with lipoxygenase present in tomato homogenisate.When 18O2-labeled (9S)-LOOH (2) was used 18O was found in the terpene epoxide.While 3 is converted under physiological conditions regioselectivity in high yield into its 4,5-epoxide 4, the yield of epoxidized products from long-chain molecules, e.g. squalene (8), decreases strongly and no regioselectivity was observed. - Key Words: Terpenes/ Epoxides/ Linoleic acid derivatives/ Hydroperoxides/ Labeled compounds, 18O2
