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- W2039481503 abstract "Ireland–Claisen rearrangement of the nine-membered macrolide 22 leads stereospecifically to the tetrahydrofurancarboxylate 23, via the boat-like transition state 9. The hydroxy-acid precursor 21c to the macrolide 22 has been prepared by Michael addition of the sodium alkoxide of (Z)-allylic alcohol 20 to methyl acrylate in the presence of dimethyl sulfoxide. Subsequent conversion into the corresponding aldehyde 29, Grignard addition, cleavage of the alkene and acid-catalysed cyclisation gives (±)-sesamin 32. The epimeric ester 33 has been converted into (±)-samin 37 by related functional group manipulations, but excluding the Grignard coupling, and a final isomerisation." @default.
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- W2039481503 date "1998-01-01" @default.
- W2039481503 modified "2023-09-27" @default.
- W2039481503 title "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" @default.
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- W2039481503 doi "https://doi.org/10.1039/a801667d" @default.
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