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- W2493276390 abstract "AM-Toxin I (I, Scheme 1) is a host specific phytotoxin. To elucidate the role of the double bond in the ΔAla2 residue, we planned to prepare [L-Ala2]- or [D-Ala2]-AM-toxin I (II) by hydrogenation of AM-toxin I. By way of a preliminary study we hydrogenated cyclo(ΔAla-L-Leu) (III) and observed unexpectedly high asymmetric induction, affording pure cyclo(L-Ala-L-Leu) (IV). Scheme 1 Cyclo(L-Ser-L-AA) (AA=Ala, Val, Phe or Lys(ε-Ac)) was converted by the Photaki method (1) into the corresponding cyclo (ΔAla-L-AA) and subsequently hydrogenated with Pd black in methanol at 25°C affording cyclo(Ala-L-AA) (2). Generally high chiral inductions defined as %L-Ala minus %D-Ala in the cyclo(Ala-L-AA) were observed, ranging from 92 to 98% with yields of 63-75%. Similarly high chiral inductions (96-99%) were observed for hydrogenation of a series of cyclo(ΔAA'-L-AA) (ΔAA'=ΔAba, ΔVal or ΔLeu) prepared from cyclo(Gly-L-AA) and appropriate aldehydes (3). Hydrogenation of ΔPhe or ΔTrp in cyclo(ΔPhe or ΔTrp-L-AA) resulted in a slightly lower asymmetric" @default.
- W2493276390 created "2016-08-23" @default.
- W2493276390 creator A5001275408 @default.
- W2493276390 date "1982-04-28" @default.
- W2493276390 modified "2023-09-26" @default.
- W2493276390 title "Asymmetric Hydrogenation of Cyclic Dipeptides Containing α,β-Dehydroamino Acid Residues and Subsequent Preparation of Optically Pure α-Amino Acids" @default.
- W2493276390 doi "https://doi.org/10.1021/bk-1982-0185.ch022" @default.
- W2493276390 hasPublicationYear "1982" @default.
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