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An enantioselective synthesis of the natural alkaloid (-)-indolizidine 167B is described. From an easily accessible chiral cycloheptene derivative a 2,5-dihydropyrrolidine was formed via a ruthenium-catalysed tandem ring-rearrangement metathesis. Annellation of the second ring was effected by an intramolecular reductive amination step under complete stereocontrol. (-)-Indolizidine 167B was obtained...
A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters...
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