Structures of angrendiol, ferolin, and chimganidin
SummaryOn the basis of the results of a study of the products of chemical transformations and spectra, the structure of angrendiol has been established as 4,8-dihydroxygermacra-1(10), 5(6)-diene. It has been shown that ferolin and chimganidin are monoesters of angrendiol with parahydroxybenzoic and vanillic acids, respectively, at the secondary hydroxy group.
Cope rearrangement of some germacrane-type furan sesquiterpenes. Part I
Cope rearrangements of some germacrane-type furan sesquiterpenes have been examined and the absolute configuration of the rearrangement products has been confirmed. The results suggest that the stereochemistry of the rearrangement product is controlled by the conformation of the ten-membered ring compound.
Conformations of 10-membered rings in bicyclogermacrene and isobicyclogermacrene
Abstract The configurations of the endocyclic double bonds and the conformations of 10-membered rings in bicyclogermacrene (1) and isobicyclogermacrene (3), sesquiterpenes containing a fused 1,1′- dimethylcyclopropane ring, have been elucidated in solution by the use of intramolecular nuclear Overhauser effects. Compounds 1 and 3 adopt conformations A and C, respectively; the double bonds of the former have trans,trans-orientation, and those of the latter trans,cis-orientation.