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Chemical and Pharmaceutical Bulletin
Vol. 43 (1995) No. 10 P 1617-1620

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http://doi.org/10.1248/cpb.43.1617


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.

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