LYCOPODIUM ALKALOIDS: XVI. ANNOTINE

Abstract

Annotine, C16H21O3N, is shown to be pentacyclic and to contain a tertiary hydroxyl group, a lactone function, a tertiary nitrogen atom, and a dialkylated double bond. The position of the double bond and the tertiary hydroxyl group relative to the nitrogen atom has been established by Emde degradation of annotine methiodide. The presence of a lactone function is inferred from the reduction of annotine to dihydroannotinol, a hemiacetal, which reacts with 1 mole of ethyl mercaptan. The reduction of the lactone to a diol in an annotine derivative has been carried out. The chemical studies and the examination of annotine and its derivatives by modern instrumental methods allow the assignment of a plausible structure to the alkaloid.