146610-75-5Relevant academic research and scientific papers
FIRST SYNTHESIS OF LYCOPERDIC ACID
Kaname, Mamoru,Yoshifuji, Shigeyuki
, p. 8103 - 8104 (1992)
Lycoperdic acid, (2S,2'S)-2-amino-3-(2'-carboxy-5'-oxo-2'-tetrahydrofuranyl)propanoic acid, was synthesized from trans-4-hydroxy-L-proline.
Asymmetric synthesis of lycoperdic acid
Yoshifuji,Kaname
, p. 1617 - 1620 (2007/10/03)
Lycoperdic acid [(2S,5'S)-2-amino-3-(5'-carboxy-2'-oxo-5'- tetrahydrofuranyl)propanoic acid], isolated from the mushroom Lycoperdon perlatum, was synthesized from trans-4-hydroxy-L-proline by a six-step route involving samarium diiodide (SmI2)-mediated formation of the spiro-γ- lactone and ruthenium tetroxide (RuO4) oxidation of the L-proline ring system to the L-pyroglutamic acid moiety. Lycoperdic acid (1) was found to undergo hydrolysis of the γ-lactone ring in 1 N hydrochloric acid at 23°C, giving an equilibrated mixture of 1 and the corresponding hydroxy acid.
