Carballeira N M, Emiliano A, Hernández-Alonso N, González F A
Department of Chemistry, University of Puerto Rico, P. O. Box 23346, San Juan, Puerto Rico 00931.
J Nat Prod. 1998 Dec;61(12):1543-6. doi: 10.1021/np980274o.
The total synthesis of the naturally occurring (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid was accomplished using as a key step Mukaiyama's trimethylsilyl cyanide addition to 4- and 5-pentadecenal, respectively. These syntheses further confirm the structures of the natural marine fatty acids and corroborate their cis double-bond stereochemistry. The title compounds were antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 0.35 micromol/mL) and Streptococcus faecalis (MIC 0.35 micromol/mL).
天然存在的（Z）-2-甲氧基-5-十六碳烯酸和（Z）-2-甲氧基-6-十六碳烯酸的全合成得以实现，关键步骤分别是向4-和5-十五碳烯醛中加入武田的三甲基硅基氰化物。这些合成进一步证实了天然海洋脂肪酸的结构，并确证了它们的顺式双键立体化学。标题化合物对革兰氏阳性菌金黄色葡萄球菌（最低抑菌浓度0.35微摩尔/毫升）和粪肠球菌（最低抑菌浓度0.35微摩尔/毫升）具有抗菌活性。
