Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid.
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).
Carballeira
N M
NM
Department of Chemistry, University of Puerto Rico, P. O. Box 23346, San Juan, Puerto Rico 00931. ncarball@upracd.upr.clu.edu
Emiliano
A
A
Hernández-Alonso
N
N
González
F A
FA
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
C117236:2-methoxy-5-hexadecenoic acid; C117235:2-methoxy-6-hexadecenoic acid; D000900:Anti-Bacterial Agents; D005229:Fatty Acids, Monounsaturated