Getting the most out of sulfur. Enantiopure epoxyvinyl sulfone 1 is transformed to syn‐ and anti‐dienyl sulfones 2 and 3, respectively, by means of a nucleophilic methylation/sulfenylation/directed elimination reaction sequence. Compound 2 has been converted into termini‐differentiated seven‐carbon polypropionate segments found in five biologically significant natural products.
Bestleistungen dank Schwefel: Durch eine Reaktionssequenz aus nucleophiler Methylierung, Sulfenylierung und Eliminierung wird das enantiomerenreine Epoxyvinylsulfon 1 in die syn‐ oder anti‐Dienylsulfide 2 bzw. 3 umgewandelt. Das vielseitige Intermediat 2 kann auch als siebenatomiges Synthon für die Polypropionat‐Einheiten von fünf wichtigen Naturstoffen verwendet werden.
Rings with 7 or more membersRings with 7 or more members Q 0050 Functionality Propagation by Alkylative Oxidation of Cross-Conjugated Cycloheptadienyl Sulfones. -The methodology allows the stereospecific functionalization of all 7 carbon centers. The products are precursor of various antibiotic segments. -(TORRES, E.; CHEN, Y.; KIM, I. C.; FUCHS*, P. L.; Angew.
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