Isolierung von (2S, 4S)‐(+)‐γ‐Hydroxynorvalin und (2S, 4R)‐(−)‐γ‐Hydroxynorvalin aus Boletus satanas Lenz

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Abstract
We have isolated from the carpophores of Boletus satanas Lenz (Basidiomycetae) (2S,4S)‐(+)‐γ‐hydroxynorvaline (1) and (2S,4R)‐(−)‐γ‐hydroxynorvaline (2). The chirality of each diastereomer has been determined by chemical synthesis starting from optically active precursors and by application of different chiroptical methods. Gaschromatographic separation of the derived diastereomeric N‐[(S)‐α‐methoxypropionyl]‐lactones reveals that the optical purity of natural 2 is 88% whereas 1 exists as a partial racemate: (2S,4S): (2R,4R) = 3:2.Muscarine could not be detected in the carpophores of B. satanas, contrary to some literature data but basic substances of unknown structure are present in low concentration.