title: Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ(8)-THC, and Analogues.
abstract: Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising a stereoselective hydroboration followed by oxidation or reduction of the corresponding intermediary boranes. The divergent approach is convincingly demonstrated by the five-step syntheses of (+)-machaeriol B, (+)-machaeriol D, and related analogues, and the four-step synthesis of (+)-Δ(8)-THC and an analogue.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany).
authors.forename: Felix
authors.initials: F
authors.lastname: Klotter
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany). studer@uni-muenster.de.
authors.forename: Armido
authors.initials: A
authors.lastname: Studer
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D001688:Biological Products; C440676:machaeriol B; C000604136:machaeriol D; C035731:delta-8-tetrahydrocannabinol; D010165:Palladium; D013759:Dronabinol
keywords: cannabinoids; decarboxylative couplings; divergent synthesis; natural products; total synthesis