title: Stereoselective Total Syntheses of Polyacetylene Plant Metabolites via Ester-Tethered Ring Closing Metathesis.
abstract: Total syntheses of five naturally occurring polyacetylenes from three different plants are described. These natural products have in common an E,Z-configured conjugated diene linked to a di- or triyne chain. As the key method to stereoselectively establish the E,Z-diene part, an ester-tethered ring-closing metathesis/base-induced eliminative ring opening sequence was used. The results presented herein do not only showcase the utility of this tethered RCM variant but have also prompted us to suggest that the originally assigned absolute configurations of chiral polyacetylenes from Atractylodes macrocephala should be revised or at least reconsidered.
authors.affiliation: Universität Potsdam , Institut für Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
authors.forename: Bernd
authors.identifier: 0000-0002-0224-6069
authors.initials: B
authors.lastname: Schmidt
authors.affiliation: Universität Potsdam , Institut für Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Audörsch
mesh_terms: D031174:Atractylodes / Q000737:chemistry* / Q000378:metabolism; D003500:Cyclization; D004952:Esters / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D053279:Polyynes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D004952:Esters; D053279:Polyynes