The carbonyl chemistry of tutin and its derivatives

Abstract

Tutin is the poisonous principle found in the leaves, stem and berries of members of the natural order Coriariae, three of which are native to New Zealand: C. ruscifolia, C. thymofolia, C. augustissima. Easterfield and Aston originally isolated tutin T.H. Easterfield and B.C. Aston, J., 1901, 79, 120, from the species c. ruscifolia, which is that shrub commonly known as "Tutu" or "Tute" and is by far the best known of the three. Japanese workers also have isolated tutin along with coriamyrtin Kinoshita, J.C.S. Japan, 1930, 51, 99, Idem, ibid., 1931, 52, 171, Kariyone and Sato, J. Pharm. Soc. Japan, 1930, 50, 659, Idem, ibid., 1930, 51, 134, and other related compounds, in the leaves of Coriariae japonica, a species indigenous to Japan. Tutin, resembling the rest of the amaroid group has the property of extreme physiological activity, similar to that of strychnine. The absence of nitrogen coupled with their high oxygen content has often caused these compounds to be referred to as the oxygen alkaloids. Previous work on the chemical nature of tutin is best dealt with under the headings of the various functional groups already identified in the molecule, but first the nature of the carbon skeleton must be discussed.