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

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.