Synthesis of enantiomerically pure β-amino-α-methylene-γ-butyrolactones by way of ozonolysis of aromatic α-amino acids

Abstract

The (R) and (S) isomers of β-amino-α-methylene-γ-butyrolactone hydrochloride (4-amino-dihydro-3-methylene-2(3H)-furanone hydrochloride) have been synthesized from (R)- and (S)-tryptophan, respectively. A key step is the ozonolysis of N,O-diacetyl-2-amino-3-(3′-indolyl)-1-propanol. (S)-β-Amino-α-methylene-γ-butyrolactone hydrochloride has been synthesized also by an analogous route starting with (S)-phenylalanine.