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Issue 6, 1997
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Diastereospecific approach to (±)-samin and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane (furofuran) lignans using the Ireland–Claisen rearrangement of unsaturated oxamacrolides

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-sulfonyl cinnamate 26 and lactonization of the derived hydroxy acid 27c using Mukaiyama’s reagent. Subsequent oxidative cleavage of the vinyl group in the tetrahydrofuran 30 gives (±)-samin 9, a precursor of both symmetrical and unsymmetrical furofuran lignans 8.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 857-864
Article type
Paper

Diastereospecific approach to (±)-samin and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane (furofuran) lignans using the Ireland–Claisen rearrangement of unsaturated oxamacrolides

H. M. Hull, N. Bradley and D. W Knight, J. Chem. Soc., Perkin Trans. 1, 1997, 857
DOI: 10.1039/A606545G

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