ABSTRACT
Daphnane polyol esters have been found in members of both the families Euphorbiaceae and Thymelaeaceae, but appear to be more widely distributed in the latter family. This provides evidence for a close relationship between these two families. A number of daphnane polyol esters have had their structures elucidated unequivocally by X-ray crystallographic methods. As a group, the daphnane-type polyol esters are structurally more varied and interesting than either the tiglianes or the ingenanes. Perhaps as unusual as the orthoester function is the more recently characterized 1α-alkyldaphnane type of structure. Resiniferonol esters group of daphnane derivatives most closely resembles the classical phorbol-type. A few resemble the daphnetoxin type compounds in all but two features. First, the long-chain aliphatic orthoester is attached at its sub-terminal carbon atom to C-1 of the daphnane nucleus, producing a macrocyclic fourth ring. Secondly, and probably as an inevitable result of macrocyclic cyclization, the Δ1,2 bond is saturated.
