Nm. Carballeira et al., 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, 61(12), 1998, pp. 1543-1546
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 natura
l 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 mu mol/mL) and Streptococcus faecalis (MIC
0.35 mu mol/mL).