Studies on the Chemistry of Annotinine

Abstract

The amino acid C14H19O4N, obtained from annotinine by oxidative fission of ring A, has been converted to the o,N-diacetyl acyclic anhydride C18H22O6N, and the anhydride ring has been shown to be five-membered. Oxidation studies have been carried out on the N-methyl lactone C17H27O2N, obtained by fission of ring A, and the oxidation products isolated and characterized. Hofmann degradation studies on the N-methyl lactone have been carried out and the products isolated from this reaction are discussed in relation to the known structure of the alkaloid.