Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid

J Nat Prod. 1998 Dec;61(12):1543-6. doi: 10.1021/np980274o.

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).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Enterococcus faecalis / drug effects
  • Fatty Acids, Monounsaturated / chemical synthesis*
  • Fatty Acids, Monounsaturated / isolation & purification
  • Gram-Negative Bacteria / drug effects*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Spectrophotometry, Infrared
  • Staphylococcus aureus / drug effects

Substances

  • 2-methoxy-5-hexadecenoic acid
  • 2-methoxy-6-hexadecenoic acid
  • Anti-Bacterial Agents
  • Fatty Acids, Monounsaturated