The present study describes a new synthesis of (-)-(R)-and (+)-(S)-angustureine enantiomers, as well as of racemate (±)-angustureine, from a racemic β-amino ester controlled by kinetic enzymatic resolution. This strategy allowed to incorporate the basic skeleton, as well as to control the single stereocenter at carbon 2 in both enantiomers. The sequence of five steps starting from the chiral β-amino ester and sodium carboxylate for the synthesis of both alkaloids achieved overall yields of 80 and 44%, respectively, and produced excellent enantiomeric excesses (95 and 96%, respectively) with no protection of functional groups in any of the steps.
angustureine; β-amino ester; enzymatic resolution; quinoline alkaloid
