Abstract
AbstractThe crystal structure of (−)‐corycavinium (+)‐10‐camphorsulfonate has been investigated by X‐ray analysis. The structure of (−)‐corycavinium ion ( (−)‐(7S,13S,14R)‐5,6,13,13a‐tetrahydro‐13a‐hydroxy‐7‐methyl‐2,3;9,10‐bis(methylenedioxy)‐8H‐dibenzo[a,g]quinolizinium), has been determined. The conformation with B/C‐cis‐conjunction, a twisted half‐chair of ring B, and a half‐chair of ring C, as well as α‐oriented substituted groups N…Me, C…Me, and C…OH is revealed. Feeding experiments with cell suspension cultures of Corydalis incisa (Papaveraceae) defined the intermediacy of (−)‐corycavinium in the route from protoberberine‐type to hexahydrobenzo[c]phenanthridine‐type of alkaloids. On the basis of the present crystal conformation, the stereospecificity of the relating enzyme is biogenetically considered.
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