Oncinotis inandensis

In the course of the structure elucidation of the natural occurring spermidine alkaloides such as inandeninone 11/108, (Scheme 11/15) the Schmidt reaction played an important role. The alkaloid is a nearly 1 1 mixture of two isomers, isolated from Oncinotis inandensis Wood et Evans. To make sure that the compounds differed only in the location of the carbonyl group at positions C(12) and C(13), the mixture was treated with sodium azide, sulfuric acid, and chloroform. The product consisted of a mixture of four ring enlarged dilactams (one of them, compound 11/109, is shown) with nearly equal ratios [84],... 

The synthesis of desoxoinandenine (VII/108) represents an application of this lactam formation process [55] [56], Scheme VII/21. Desoxoinandenine is a reduction product of the natural spermidine alkaloid inandeninone from Oncinotis inandensis Wood et Evans [57]. 

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