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Beilstein J. Org. Chem. 2007, 3, No. 6, doi:10.1186/1860-5397-3-6
Graphical Abstract
Scheme 1: Synthesis using a Temporary Connection Strategy.
Scheme 2: Intramolecular allylation of aldehyde 1 generates two out of the four possible oxasilacycles. The b...
Scheme 3: The effect of introducing a methyl group α- to the aldehyde in the cyclisation precursor will depen...
Scheme 4: Retrosynthesis of aldehyde anti-4.
Scheme 5: Attempts to reduce the bulky aryl ester resulted in Si-O bond cleavage and over-reduction to the pr...
Scheme 6: Preparation of syn- and anti-β-hydroxy esters.
Scheme 7: Preparation of the syn- and anti-aldehyde cyclisation precursors 4.
Scheme 8: Intramolecular allylation results.
Figure 1: nOe data for the two oxasilacycles obtained from allylation of aldehyde anti-4b.