title: Divergent diastereoselective synthesis of iridomyrmecin, isoiridomyrmecin, teucrimulactone, and dolicholactone from citronellol.
abstract: The iridoid natural products iridomyrmecin, isoiridomyrmecin, teucriumlactone, and dolicholactone were prepared from citronellol using a divergent diastereoselective approach. Key steps include a highly diastereoselective enamine/enal cycloaddition and the selective reduction of masked aldehyde functionalities by ionic hydrogenation.
authors.affiliation: Department of Chemistry, Kenyon College, Gambier, Ohio 43022, United States.
authors.forename: Clara J
authors.initials: CJ
authors.lastname: Fischman
authors.forename: Snow
authors.initials: S
authors.lastname: Adler
authors.forename: John E
authors.initials: JE
authors.lastname: Hofferberth
mesh_terms: D000080462:Acyclic Monoterpenes; D039823:Iridoids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080462:Acyclic Monoterpenes; D039823:Iridoids; D039821:Monoterpenes; C575113:isoiridomyrmecin; C575112:iridomyrmecin; C007078:citronellol