146554-64-5Relevant articles and documents
Diastereoselective synthesis of glutamate-appended oxolane rings: Synthesis of (S)-(+)-lycoperdic acid
Cohen, Jamie L.,Chamberlin, A. Richard
, p. 9240 - 9247 (2008/03/14)
(Chemical Equation Presented) The stereocontrolled synthesis of the glutamate-containing natural product (S)-(+)-lycoperdic acid is described. The key transformation in the synthetic route was an efficient diastereoselective annulation of an oxolane ring
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.