Diastereospecific approach to (±)-samin and 2, 6-diaryl-3, 7-dioxabicyclo [3.3. 0] octane (furofuran) lignans using the Ireland–Claisen rearrangement of unsaturated …

HM Hull, DW Knight

Index: Hull, Hilary M.; Knight, David W. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 857 - 863

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Abstract

Enolate Claisen rearrangement of the unsaturated oxamacrolide 28 leads specifically, after reduction, to the tetrahydro-3-furylmethanol 30, via a boat-like transition state 29. Initial attempts to obtain a macrolide related to 28 by O-alkylation of the model β-hydroxy ester 12 using acetimidate 13 were inefficient. Key steps in the successful preparation of the macrolide 28 are Michael addition of a mono-protected (Z)-but-2-ene-1, 4-diol 23 to an α- ...