186670-53-1Relevant articles and documents
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.
Synthesis of Saturated Anacardic Acids, and Alkenyl and Alkynyl Analogues
Tyman, John H. P.,Visani, Naina
, p. 228 - 240 (2007/10/03)
The C-alkylation of esters of 2-methoxy-6-methylbenzoic acid and of the 4-methyl isomers affords a route to homologous compounds including in the former case members of the natural anacardic acids from Anacardium occidentale and ω-alkynyl compounds suitable for synthesising other natural phenolic lipids or for structure/activity studies.
