REACTIONS OF OXODELCOSINE AND INTERRELATION OF DELCOSINE AND DELSOLINE

Abstract

The oxidation of diacetyldelcosine produces a lactam which, after hydrolysis of the acetyl groups, can be oxidized further to a diketo-lactam in which one of the keto groups is in a five- and the other in a six-membered ring. This result leads to an alteration of the previously suggested structure of delcosine. The new structure suggests a close relationship between delcosine and delsoline which is confirmed by the methylation of the former. The reaction is selective and gives rise to a monomethyldelcosine identical in every way with delsoline. Reduction of the diketo-lactam (didehydro-oxodelcosine) with sodium borohydride gives oxodelcosine. Dehydro-oxodelcosine is also described, and its oxidation with lead tetraacetate as well as that of oxodelcosine lead to the formation of keto-products which lend supporting evidence for the structure assigned to delcosine.