TETRAHYDROFURAN-TYPE TERPENOIDS FROM TANACETUM VULGARE

Article abstract of DOI:10.1016/S0031-9422(00)84096-0

Investigation of a rare genotype of Tanacetum vulgare afforded a series of tetrahydrofuran-type terpenoids, whose pattern was different in flowers and leaves.The major constituent of the flowers was the trans Δ^3,4-hydroperoxide of davanone, whereas the leaves gave mostly a peroxyhemiketalic compound resulting from the intramolecular cyclization of the cis Δ^3,4-hydroperoxide of davanone.Structures were elucidated by spectral data and chemical reactions, including correlation with natural (+)-davanone.The peroxyhemiketalic compound upon acylation of its hydroxyl group gave an instantaneous complex reaction, resulting in the formation of a β-acyloxyenone and loss of one molecule of acetone.Among the minor constituents of the leaves, a C-10 carboxylic acid biogenetically related with davanone was isolated.Key Word Index - Tanacetum vulgare; Compositae; sesquiterpenes; davanone; hydroperoxides; peroxyhemiketals; chemotaxonomy.