2-アミノアルコール系キラル合成子の開発と応用

抄録

The 2-oxazolone heterocycle is proved of synthetic potential as a building block for 2-amino alcohol structures, which are found in a substantial number of bioactive compounds such as enzyme inhibitors, antibiotics and sympathomimetic amines. The synthetic strategy consists of the following steps : (1) the diastereoselective introductions of easily replaceable groups (X, Y) to the olefinic moiety of the 2-oxazolone, (2) stereospecific and stepwise substitution of X and Y with appropriate groups and (3) the opening of the 2-oxazolidone ring system under mild condition.
Methoxybromination (Br₂/MeC (OMe) ₃) and methoxyselenylation (PhSeCl/MeOH) of 3- (2-exo-alkoxy apocamphanecarbonyl) -2-oxazolone proceed smoothly to result in highly stereoselective formation of chiral synthons for 2-amino alcohols, but with opposite π-facial selectivity Effective conversion of these adducts to biologically significant 2-amino alcohols such as statine and β-hydroxyglutamic acid is described.