Structure, chemistry and stereochemistry of rastevione, a sequiterpenoid from the genus stevia

Abstract

The structure and relative stereochemistry of rastevione ( 1a), the main constituent of the roots of S. serrata and S. rhombifolia, were deduced from chemical transformations combined with spectral data and by a single crystal X-ray diffraction study of rastevione acetate ( 1b). Chemical correlation of a rastevione derivative with a molecule thought to have structure IVb, suggests the structures of several previously described longipinene and longipinane derivatives, should be revised. The behaviour of longipinane-7α,8β,9β-triol-l-one in the presence of periodic acid was studied, and the structure of the reaction product established from deuterium labeling experiments showed the 7α,8β diol split.