title: Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A.
abstract: The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduced using a selective 1,4-addition. A further key step of the synthesis was the homologation of a Wieland-Miescher ketone derivative to establish the 7-membered ring.
authors.affiliation: Institute for Organic Chemistry, Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany.
authors.forename: Bettina
authors.initials: B
authors.lastname: Werner
authors.affiliation: Institute for Organic Chemistry, Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany.|Helmholtz Centre for Infection Research (HZI) , Inhoffenstrasse 7, D-38124 Braunschweig, Germany.
authors.forename: Markus
authors.identifier: 0000-0003-4858-3957
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D000473:Alkanes; D006018:Glycols; D015394:Molecular Structure; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry*
chemical_list: D000473:Alkanes; D006018:Glycols; D014315:Triterpenes; C000621940:pinacol; C558501:schiglautone A; C094074:tridecane