The use of (S)-(-)-1-(1-naphthyl)ethylamine as a resolving agent for alpha-methoxy fatty acids

A general method was developed for the diastereoselective resolution of alp ha-methoxy fatty acids utilizing (S)(-)-1-(1-naphthyl)ethylamine as resolvi ng agent. The diastereomeric amides can be easily separated by silica gel c olumn chromatography and/or capillary gas chromatography, thus allowing for a preparative and analytical method for determining the enantiomeric purit y of naturally occurring and/or synthetic alpha-methoxy fatty acids. The fi rst synthesis of the naturally occurring (R)-2-methoxyhexadecanoic acid was also accomplished in four steps starting from commercially available (+/-) -2-hydroxyhexadecanoic acid. (C) 1999 Elsevier Science Ltd. All rights rese rved.