The structure and conformation of umbellifolide, a 4,5-secoeudesmane derivative
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 2705-2709
- https://doi.org/10.1039/p19830002705
Abstract
Umbellifolide (3) is the first 4,5-secoeudesmane derivative discovered in nature. Its structure and conformation have been determined by physical methods, including X-ray analysis. Umbellifolide, both in solution and in the solid state, exists as a θ= 60° boat cyclohexanone rotamer. The exo-methylene γ-lactone group, cis-closed at C(8), is almost planar and belongs to the pseudo-rotational P-type. The X-ray determination was based on 1 047 diffractometer intensities and the least-squares refinement converged to R= 0.046. A possible biogenesis of umbellifolide from a Δ4,5-eudesmane precursor (5)via fragmentation of 4-hydroxy-5-hydroperoxyeudesmane intermediates is proposed.This publication has 4 references indexed in Scilit:
- The structure of hallerol, a boat-boat germacrane lactolJournal of the Chemical Society, Perkin Transactions 1, 1983
- The structure and chemistry of hallerin, a mixture of anomeric sesquiterpenoids from Laserpitium halleri Crantz subsp. halleriJournal of the Chemical Society, Perkin Transactions 1, 1983
- Sesquiterpene lactones from Artemisia genipi Weber: isolation and determination in plant material and in liqueursJournal of Agricultural and Food Chemistry, 1982
- Sesquiterpene lactones of Hymenoxys insignis. X-ray analyses of hymenograndin and hymenosigninThe Journal of Organic Chemistry, 1980