92116-29-5Relevant academic research and scientific papers
Synthesis of 4,8-Bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclooctan-2-ones and Determination of their Relative Configuration via Long-range
Quideau, Stephane,Ralph, John
, p. 653 - 660 (1993)
A short synthesis of the furofuranoid lignan, 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclooctan-2-one (MEL), was accomplished via a simple regioselective hydride reduction of the dilactone parent octane-2,6-dione>, followed by deoxygenation of the lactone-lactol intermediate via silane hydride transfer.The 4-trans-8-cis(iso-MEL) and the 4-cis-8-trans(epi-MEL) isomers, and a fourth related compound, featuring a 3-fused 5-membered ring skeleton were additionally formed.All four compounds were fully characterized by use of 1D and 2D NMR techniques.Examination of the long-range coupled proton network by delayed COSY experiments allowed determination of the relative configuration of these 4,8-diaryl-3,7-dioxabicyclooctan-2-one structures.The pathways followed by these long-range proton couplings and implications of the long-range and vicinal couplings with respect to favoured conformations are discussed.
Synthesis and 1H N.M.R. Spectroscopic Analysis of Some 3,7-Dioxabicyclooctane Lignans
Velde, Vincent Vande,Lavie, David,Gottlieb, Hugo E.,Perold, Guido W.,Scheinmann, Feodor
, p. 1159 - 1164 (2007/10/02)
Within the framework of a synthetic project towards the preparation of the natural germination inhibitor 2,6-diaryl-3,7-dioxabicyclooctane, several molecules with the same bicyclic skeleton were prepared and their 1H n.m.r. spectra are described in detail.For the symmetrical systems particularly, the spectra exhibited second-order features and were interpreted analytically or, when necessary, by computer simulation.These n.m.r. data enabled a conformational analysis of the ring system.
