000171732 001__ 171732
000171732 005__ 20181203022539.0
000171732 0247_ $$2doi$$a10.1021/jo102035d
000171732 02470 $$2ISI$$a000286577400011
000171732 037__ $$aARTICLE
000171732 245__ $$aTotal Asymmetric Syntheses of beta-Hydroxy-delta-lactones via Umpolung with Sulfur Dioxide
000171732 269__ $$a2011
000171732 260__ $$c2011
000171732 336__ $$aJournal Articles
000171732 520__ $$aCyclic 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.
000171732 6531_ $$aModular Polyketide Synthase
000171732 6531_ $$aPrecursor-Directed Biosynthesis
000171732 6531_ $$aRing-Closing Metathesis
000171732 6531_ $$aMarine Natural-Products
000171732 6531_ $$aEnantioselective Synthesis
000171732 6531_ $$aPrelactone-B
000171732 6531_ $$aErythromycin Biosynthesis
000171732 6531_ $$aStereoselective-Synthesis
000171732 6531_ $$aPolypropionate Synthesis
000171732 6531_ $$aAntibiotic Kendomycin
000171732 700__ $$0242650$$aExner, Claudia J.$$g171963$$uEcole Polytech Fed Lausanne, Swiss Fed Inst Technol Lausanne, Lab Glycochem & Asymmetr Synth LGSA, CH-1015 Lausanne, Switzerland
000171732 700__ $$aLaclef, Sylvain$$uEcole Polytech Fed Lausanne, Swiss Fed Inst Technol Lausanne, Lab Glycochem & Asymmetr Synth LGSA, CH-1015 Lausanne, Switzerland
000171732 700__ $$aPoli, Florent$$uEcole Polytech Fed Lausanne, Swiss Fed Inst Technol Lausanne, Lab Glycochem & Asymmetr Synth LGSA, CH-1015 Lausanne, Switzerland
000171732 700__ $$0240874$$aTurks, Maris$$g148638$$uRiga Tech Univ, Fac Mat Sci & Appl Chem, LV-1048 Riga, Latvia
000171732 700__ $$0240222$$aVogel, Pierre$$g123681$$uEcole Polytech Fed Lausanne, Swiss Fed Inst Technol Lausanne, Lab Glycochem & Asymmetr Synth LGSA, CH-1015 Lausanne, Switzerland
000171732 773__ $$j76$$q840-845$$tJournal Of Organic Chemistry
000171732 909C0 $$0252076$$pLGSA$$xU10111
000171732 909CO $$ooai:infoscience.tind.io:171732$$pSB$$particle
000171732 937__ $$aEPFL-ARTICLE-171732
000171732 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000171732 980__ $$aARTICLE