Abstract
By reacting the known 16α-bromo-N-cyano-22,26-epimino-cholestanes (e.g.2) with NaN3 inDMF 16β-azido-N-cyano-22,26-epimino-cholestanes (e.g.4) were obtained. Reduction of4 with LiAlH4 gives 16β-amino-22,26-epimino-cholestane (9). Some acylated derivatives of9 are described, e.g. the known derivatives11 and13, which prove the stereochemistry at C-16.
Similar content being viewed by others
Literatur
K. Schreiber, in:R. H. F. Manske (Hrsg.), The Alkaloids, Vol. X, S. 1ff. 1968.
J. A. Beisler undY. Sato, J. Chem. Soc. (C)1971, 149.
Vgl.G. Sayers undR. H. Travis, in:S. Goodmann undA. Gilman (Hrsg.), The Pharmacological Basis of Therapeutics, 4. Aufl., S. 1627f.
G. Schramm, Österr. Patent Nr. 295 054, Chemie Linz AG.
R. Franzmair, in Vorbereitung.
G. Adam undK. Schreiber, Chem. Ber.99, 2275 (1966).
G. Spiteller undM. Spiteller-Friedmann, Mh. Chem.96, 104 (1965).
K. Steinfelder, R. Tümmler, G. Adam undK. Schreiber, J. prakt. Chem.313, 1051 (1971).
D. B. Murphy, J. Org. Chem.19, 1807 (1954).
Author information
Authors and Affiliations
Additional information
Herrn Prof. Dr.K. Kratzl mit den besten Wünschen zum 60. Geburtstag von der Abteilung für Pharmazeutisch-chemische Forschung der Chemie Linz AG gewidmet.
Rights and permissions
About this article
Cite this article
Franzmair, R. Synthese von (22R,25S)-16β-Amino-22,26-epiminocholestanen. Monatshefte für Chemie 107, 501–510 (1976). https://doi.org/10.1007/BF00906880
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00906880