6879-76-1Relevant articles and documents
Stereoselective Transformation of the Alkaloid Lycorine to O-Demethylungiminorine and Ungiminorine
Toda, Jun,Sano, Takehiro,Tsuda, Yoshisuke,Itatani, Yoshitaka
, p. 1322 - 1332 (2007/10/02)
Diacetyllycorine, an Amaryllidaceae alkaloid, was transformed stereoselectively to the more heavily oxygenated congener, O-demethylungiminorine, by a route similar to that suggested for the biosynthesis of narcissidine.Similarly, acetylhippamine was converted to ungiminorine.A method of high yield conversion of lycorine to hippamine is also described. - The above transformations constitute a formal total synthesis of ungiminorine.Keywords--- Amaryllidaceae alkaloid; lycorine; hippamine; ungiminorine; O-demethylungiminorine; lycorine-chlorohydrin; permanganate oxidation; phosphoryl chloride; stereoselective hydroxylation; distorted boat conformation