1055252-52-2Relevant academic research and scientific papers
N,N-acetals as N-acyliminium ion precursors: Synthesis and absolute stereochemistry of epiquinamide
Wijdeven, Marloes A.,Wijtmans, Roel,Van Den Berg, Rutger J. F.,Noorduin, Wim,Schoemaker, Hans E.,Sonke, Theo,Van Delft, Floris L.,Blaauw, Richard H.,Fitch, Richard W.,Spande, Thomas F.,Daly, John W.,Rutjes, Floris P. J. T.
supporting information; experimental part, p. 4001 - 4003 (2009/05/30)
(Chemical Equation Presented) A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction of the second ring.
