Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Synthesis of Anacardic Acids, 6-[8(Z), 11(Z)-Pentadecadienyl]salicylic Acid and 6-[8(Z), 11(Z), 14-Pentadecatrienyl]salicylic Acid
Mitsuru SATOHNaoki TAKEUCHITakeshi NISHIMURATakashi OHTASeisho TOBINAGA
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2001 Volume 49 Issue 1 Pages 18-22

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Abstract

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-[8(Z), 11(Z)-pentadecadienyl]salicylic 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.

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© 2001 The Pharmaceutical Society of Japan
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