| 摘要 |
PROBLEM TO BE SOLVED: To obtain the subject compound in high purity and yield by a simple operation, by using an optically active epichlorohydrin as a starting raw material. SOLUTION: An optically active epichlorohydrin of formula I is reacted with an alkyl magnesium halide having 1-12C main chain, and then, the reaction product is cyclized under basic conditions. Then, the cyclized compound is subjected to addition reaction with trimethylsilyl-nitrile and then treated with fluoride to afford an optically active 3-hydroxyalkane nitrile having 5-16C main chain and represented by formula II. Then, the resultant compound is treated with hydrochloric acid/a lower alcohol and further treated with a mineral acid and hydrolyzed to provide the objective 3-hydroxyfatty acid having 5-16C main chain and represented by formula III. The compound of formula III is an important intermediate for biosynthesis and metabolism of fatty acid and useful as a starting raw material for medicines and agrochemicals. The synthetic method is industrially advantageous, and especially, a hydrolytic method of the compound of formula II is extremely useful, because adverse reaction is slight and lowering of optical purity does not occur. |
