NEW EFFICIENT AND HIGHLY ENANTIO-SELECTIVE PREPARATION OF ENANTIOMORPHOUSLY PURE CYCLOPENTANE-BETA-AMINO ACID

摘要

PROBLEM TO BE SOLVED: To obtain the subject amino acid having antifungal activity in high yield, by a highly enantio-selective form, by starting a corresponding meso- dicarboxylic acid anhydride. SOLUTION: In preparing the objective amino acid of formula I (A and D are each H, a halogen, hydroxyl, etc.), (A) a meso-dicarboxylic acid of formula II is converted by using (B) an allyl alcohol of formula III (R3 to R5 are each H, a 1-5C alkyl, etc.) by an asymmetric alcoholysis in the presence of an equimolar amount of a chiral amine base present in a enantiomorphously pure form in an inert solvent through a enantiomorphously pure salt stage of formula IV (E is a chiral amine base) into a compound of formula V, further the compound is reacted with an azide compound in an inert solvent in the presence of a base and converted into a corresponding acid azide. The obtained rearranged isocyanuric acid ester of formula VI is reacted with a compound of formula II to form a compound of formula VII. Finally urethane and an ester functional group are cleft in an inert solvent in the presence of a Pd catalyst and/or phosphine and a nucleophilic auxiliary.