Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid.
11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-18(Z),11(Z)-pentadecadienyllsalicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.
Satoh
M
M
Showa Pharmaceutical Univercity, Machida, Tokyo, Japan. ms@ac.shoyaku.ac.jp
Takeuchi
N
N
Nishimura
T
T
Ohta
T
T
Tobinaga
S
S
D000475:Alkenes / Q000138:chemical synthesis*; D048729:Anacardic Acids; D012459:Salicylates / Q000138:chemical synthesis*; D013057:Spectrum Analysis
C422323:6-(8,11,14-pentadecadienyl)salicylic acid; C422322:6-(8,11-pentadecadienyl)salicylic acid; D000475:Alkenes; D048729:Anacardic Acids; D012459:Salicylates; C088115:anacardic acid