1262966-75-5Relevant academic research and scientific papers
Total asymmetric syntheses of β-hydroxy-δ-lactones via umpolung with sulfur dioxide
Exner, Claudia J.,Laclef, Sylvain,Poli, Florent,Turks, Maris,Vogel, Pierre
, p. 840 - 845 (2011)
Cyclic stereotriads and stereotetrads of the β-hydroxy-d-lactone type, e.g. prelactonesBandE, commonin polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy) penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-d-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The d-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3- dienes.
