Details

Autor(en) / Beteiligte

• 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

Titel

N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide

Ist Teil von

• Organic letters, 2008-09, Vol.10 (18), p.4001-4003

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2008

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.