- Synthesis and 1H N.M.R. Spectroscopic Analysis of Some 3,7-Dioxabicyclooctane Lignans
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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.
- Velde, Vincent Vande,Lavie, David,Gottlieb, Hugo E.,Perold, Guido W.,Scheinmann, Feodor
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p. 1159 - 1164
(2007/10/02)
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- Synthesis of 2,6-Diaryl-4,8-dihydroxy-3,7-dioxabicyclooctanes
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A series of 2,6-diaryl-4,8-dihydroxy-3,7-dioxabicyclooctanes, including 4,8-dihydroxysesamin, a naturally occurring lignan, have been prepared via the corresponding dilactones.The 1H and 13C n.m.r. spectra have been compared and the bistoluene-p-sulphonate of 4,8-dihydroxyeudesmin has been reduced by lithium aluminium hydride to give (+/-)-eudesmin.Since this synthesis does not involve ring-opened intermediates and starts from a dilactone of established structure, it represents the first unequivocal synthesis of such a lignan.
- Pelter, Andrew,Ward, Robert S.,Watson, Derrick J.,Collins, Peter,Kay, I. Trevor
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p. 175 - 182
(2007/10/02)
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