Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide

Journal of Organic Chemistry 2011
Claudia Exner, Sylvain Laclef, Florent Poli, Māris Turks, Pierre Vogel

Cyclic stereotriads and stereotetrads of the β-hydroxy-δ-lactone type, e.g. prelactones B and E, common in 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-δ-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 δ-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.

Keywords
lactones, sulfur dioxide, stereoselective synthesis
DOI
10.1021/jo102035d
Hyperlink
http://pubs.acs.org/doi/pdf/10.1021/jo102035d

Exner, C., Laclef, S., Poli, F., Turks, M., Vogel, P. Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide. Journal of Organic Chemistry, 2011, Vol.76, No.3, pp.840-845. ISSN 0022-3263. Available from: doi:10.1021/jo102035d

Publication language
English (en)