Acylation and Hydrolysis Studies

Acylation and Hydrolysis Studies.— The relative reactivities of the C-1 and C-14 oxygen functionalities in a series of lycoctonine-type diterpenoid alkaloids have been examined. Diacetyl-talatizamine (63) and triacetyl-lappaconine (64), which contain C-1 methoxyl functions, were saponified approximately three times faster than diacetyl-karakoline (12), diacetyl-talatizidine (65), and tetra-acetyl-lappaconidine (66), all of which contain C-1 acetoxy-groups. In addition, karakoline (11) and karakolidine (10) were selectively mono-acylated at C-1. From these limited data the 

The results of these studies are in agreement with the acylation/hydrolysis studies reported for delphisine.  

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