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