title: A unified strategy to ent-kauranoid natural products: total syntheses of (-)-trichorabdal A and (-)-longikaurin E.
abstract: The first total syntheses of (-)-trichorabdal A and (-)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (-)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: John T S
authors.initials: JT
authors.lastname: Yeoman
authors.forename: Victor W
authors.initials: VW
authors.lastname: Mak
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D045786:Diterpenes, Kaurane / Q000138:chemical synthesis*; D005030:Ethylenes / Q000737:chemistry; D037602:Isodon / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009795:Octanes / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
chemical_list: D001688:Biological Products; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005030:Ethylenes; D007659:Ketones; D009795:Octanes; C586658:longikaurin E; D010165:Palladium; C090066:trichorabdal A; C008223:ketene; C026728:octane