Abstract
From Corydalis incisa (+)-corynoline ( 2) was isolated together with (±)-corynoline ( 2'), which has been reported to be the major alkaloid. Optical resolution of 2' was achieved by resolving the corresponding diastereomeric esters with (-)-menthoxyacetic acid. The quaternary hydroxide of (+)-corynoline-O-acetate ( 3) was subjected to Emde degradation to afford the hydromethine base ( 5), the methiodide of which was converted by further Emde degradation into the optically active nitrogenfree product ( 6). This product was identical with the nitrogen-free product resulting from Emde degradation of (+)-14-epicorynoline ( 1), whose absolute configuration has been determined by means of an X-ray analysis. This result shows the absolute configuration of (+)-corynoline ( 2) to be 11S, 13R and 14R.
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