Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid

Journal of Chromatography. a
Akio Ichikawa, Hiroshi Ono

Abstract

To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using (S)-MalphaNP acid. As a chiral-resolving agent, MalphaNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MalphaNP esters was observed when n-hexane-THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MalphaNP esters gave (R)-2-methyl-4-heptanol and its enantiomer; enantiopure (S)-MalphaNP acid was also recovered. In addition, the preferred conformation of the MalphaNP ester was confirmed using methyl (R)-3-hydroxyvalerate as an authentic compound.

References

Apr 1, 1977·Chemical & Pharmaceutical Bulletin·J GotoT Nambara
Oct 29, 1996·Proceedings of the National Academy of Sciences of the United States of America·W S Leal
Jan 30, 2002·Bioorganic & Medicinal Chemistry·Yuichi Hashimoto
Sep 11, 2002·Enantiomer·Takuma FujitaNobuyuki Harada
Aug 4, 2004·Chirality·Akio IchikawaNobuyuki Harada

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