103904-74-1Relevant articles and documents
A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling
Weigel, William K.,Dennis, Taylor N.,Kang, Amrik S.,Perry, J. Jefferson P.,Martin, David B. C.
supporting information, p. 6234 - 6238 (2018/10/05)
A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.
Synthesis of polyunsaturated constituents of phenolic lipids
Tyman, John H.P.,Visani
, p. 157 - 174 (2007/10/03)
The diene, (ZZ)-[(8,11)-pentadecadienyl]salicylic acid, (or 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl] acid), has been synthesised by two routes. In the first, the key intermediate methyl or ethyl 2-hydroxy-6-(7-bromoheptyl)benzoate has been converted to methyl or ethyl 2-hydroxy-6-(10-hydroxydec-8-ynyl)benzoate and thence by reaction of the corresponding bromide with 1-pentynylmagnesium bromide to methyl or ethyl 2-hydroxy-6-(pentadeca-8,11-diynyl)benzoate. Selective reduction afforded methyl or ethyl 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoate. An attempt to employ the Grignard reagent from methyl 2-methoxy-6-(non-8-ynyl)benzoate and reaction with 1-bromohex-2-yne was ineffective because of a side reaction of the former with ethylmagnesium bromide to give a ketone. In the third approach ethyl 2-methoxy-6-methylbenzoate was alkylated with 1-iodotetradeca-7,10-diyne and the product selectively reduced as before to the O-methyl ether ethyl ester. A variety of C14 intermediates has been prepared for the derivation of the 8(E),11(E), 8(E),11(Z) and 8(Z),11(E) stereoisomers by the alkylation procedure. A similar methodology of alkylation can be adopted for obtaining corresponding trienes in which some progress has been made commencing with the synthesis of the 8(Z),11(Z),14 compound.
