An alternative diastereospecific approach to (±)-samin and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane [furanofuran] lignans based on the Ireland–Claisen rearrangement of unsaturated oxa-macrolides
作者： Hilary M. Hull (née Bradley , éRichard G. Jones , David W. Knight
DOI: 10.1039/A801667D
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摘要: Ireland–Claisen rearrangement of the nine-membered macrolide 22 leads stereospecifically to tetrahydrofurancarboxylate 23, via boat-like transition state 9. The hydroxy-acid precursor 21c has been prepared by Michael addition sodium alkoxide (Z)-allylic alcohol 20 methyl acrylate in presence dimethyl sulfoxide. Subsequent conversion into corresponding aldehyde 29, Grignard addition, cleavage alkene and acid-catalysed cyclisation gives (±)-sesamin 32. epimeric ester 33 converted (±)-samin 37 related functional group manipulations, but excluding coupling, a final isomerisation.
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