Exner, Claudia J.Laclef, SylvainPoli, FlorentTurks, MarisVogel, Pierre2011-12-162011-12-162011-12-16201110.1021/jo102035dhttps://infoscience.epfl.ch/handle/20.500.14299/74440WOS:000286577400011Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-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-delta-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 delta-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.Modular Polyketide SynthasePrecursor-Directed BiosynthesisRing-Closing MetathesisMarine Natural-ProductsEnantioselective SynthesisPrelactone-BErythromycin BiosynthesisStereoselective-SynthesisPolypropionate SynthesisAntibiotic Kendomycintext::journal::journal article::research article