title: Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid.
abstract: 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).
authors.affiliation: Department of Chemistry, University of Puerto Rico, P. O. Box 23346, San Juan, Puerto Rico 00931. ncarball@upracd.upr.clu.edu
authors.forename: N M
authors.initials: NM
authors.lastname: Carballeira
authors.forename: A
authors.initials: A
authors.lastname: Emiliano
authors.forename: N
authors.initials: N
authors.lastname: Hernández-Alonso
authors.forename: F A
authors.initials: FA
authors.lastname: González
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000302:isolation & purification; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: C117236:2-methoxy-5-hexadecenoic acid; C117235:2-methoxy-6-hexadecenoic acid; D000900:Anti-Bacterial Agents; D005229:Fatty Acids, Monounsaturated