title: Structure elucidation and total synthesis of kulkenon.
abstract: The impressive biological profile of secondary metabolites isolated from strains of Sorangium cellulosum prompted us to initiate synthetic studies on kulkenon, also isolated from Sorangium cellulosum. The synthesis features a syn-selective vinylogous Kobayashi aldol reaction, recently developed by us, and a ring-closing intramolecular Heck reaction as the pivotal transformations. Comparison of the NMR spectra of the authentic and synthetic material revealed that the proposed configuration had to be revised. A combination of molecular modeling and NOE experiments was used to propose the revised configuration, which was confirmed by a new synthesis.
authors.affiliation: Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany); Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, Braunschweig (Germany).
authors.forename: Gerrit
authors.initials: G
authors.lastname: Symkenberg
authors.forename: Markus
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D018942:Macrolides
keywords: Kobayashi aldol reaction; kulkenon; macrolactones; structure elucidation; total synthesis