The recently discovered marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid was synthesized for the first time in six steps (26% overall yield) starting from commercially available methyl 12-methyltridecanoate. The synthetic approach provided enough material to corroborate the structure of the acid, which was recently identified in the sponge Amphimedon complanata from Aguadilla, Puerto Rico, and to test its cytotoxicity to three leukemia cell lines. The key step in the synthesis was the addition of trimethylsilyl cyanide to 12-methyltridecanal under triethylamine catalysis. Nuclear magnetic resonance data are provided for the first time for this methoxylated fatty acid and the synthetic approach utilized is of general applicability since it can be used in the synthesis of other methyl-branched 2-methoxylated fatty acids. We also report that the acid (+/-)-2-methoxy-13-methyltetradecanoic acid is cytotoxic to human chronic myelogenous leukemia K-562 (EC50=238 microM), histiocytic lymphoma U-937 (EC50=250 microM), and promielocytic leukemia HL-60 (EC50=476 microM) in RPMI 1640 medium.

中文翻译：

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海洋脂肪酸（+/-）-2-甲氧基-13-甲基十四烷酸的首次全合成：对白血病细胞的细胞毒性脂肪酸。

最近发现的海洋脂肪酸（+/-）-2-甲氧基-13-甲基十四烷酸是从市售的12-甲基十三烷酸甲酯开始，以六个步骤（总收率26％）首次合成的。合成方法为证实酸的结构提供了足够的材料，该结构最近在波多黎各阿瓜迪亚的海绵Amphimedon complanata中被鉴定出来，并测试了其对三种白血病细胞系的细胞毒性。合成中的关键步骤是在三乙胺催化下将三甲基甲硅烷基氰化物添加到12-甲基三苯甲醛中。首次提供了该甲氧基化脂肪酸的核磁共振数据，并且所使用的合成方法具有普遍适用性，因为它可以用于合成其他甲基支链的2-甲氧基化脂肪酸。