title: Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne.
abstract: The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated 8(Z),10(E)-diene moiety was achieved through a tethered ring-closing metathesis approach, comprising a Ru-catalyzed RCM followed by a base-induced elimination. A Pd-catalyzed Cadiot-Chodkiewicz coupling was used for the synthesis of the diyne. Overall, atractylodemayne A was synthesized in nine steps for the longest linear sequence.
authors.affiliation: Universitaet Potsdam , Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany.
authors.forename: Bernd
authors.initials: B
authors.lastname: Schmidt
authors.affiliation: Universitaet Potsdam , Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Audörsch
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D053280:Diynes / Q000138:chemical synthesis* / Q000737:chemistry; D005233:Fatty Alcohols; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D053280:Diynes; D005233:Fatty Alcohols; D011090:Polyenes; C000609067:atractylodemayne A; C034379:falcarindiol