TY - JOUR
T1 - Structural biochemistry. Part VIII. 9-Amino-(9-deoxy)-cinchona alkaloids
AU - Pettit, George
AU - Gupta, S. K.
PY - 1968
Y1 - 1968
N2 - Lithium aluminum hydride reduction of the oximes derived from quinidinone (IIIa) and cinchonidinone has been used to obtain 9-amino-(9-deoxy)quinidine (IIb) and the corresponding 9-amine in the cinchonine series. Based on optical rotatory dispersion measurements, tentative stereochemical assignments for the amines have been proposed. A major objective of the present study, synthesis of 9-(benzyloxycarbonylthreonylseryl)amino-(9-deoxy)quinidine (IId) was achieved by condensing amine (IIb) with benzyloxycarbonylthreonylserine azide. In connection with the preparation of quinidinone and cinchonidinone, reaction between, e.g., quinine and acetic anhydride-dimethyl sulphoxide gave exclusively the corresponding 9-acetoxy-derivative.
AB - Lithium aluminum hydride reduction of the oximes derived from quinidinone (IIIa) and cinchonidinone has been used to obtain 9-amino-(9-deoxy)quinidine (IIb) and the corresponding 9-amine in the cinchonine series. Based on optical rotatory dispersion measurements, tentative stereochemical assignments for the amines have been proposed. A major objective of the present study, synthesis of 9-(benzyloxycarbonylthreonylseryl)amino-(9-deoxy)quinidine (IId) was achieved by condensing amine (IIb) with benzyloxycarbonylthreonylserine azide. In connection with the preparation of quinidinone and cinchonidinone, reaction between, e.g., quinine and acetic anhydride-dimethyl sulphoxide gave exclusively the corresponding 9-acetoxy-derivative.
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U2 - 10.1039/j39680001208
DO - 10.1039/j39680001208
M3 - Article
AN - SCOPUS:37049131403
SN - 0022-4952
SP - 1208
EP - 1213
JO - Journal of the Chemical Society C: Organic
JF - Journal of the Chemical Society C: Organic
ER -