title: Catalytic enantioselective total synthesis of (+)-torrubiellone C.
abstract: Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation in high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrubiellone C, which led to the assignment of the configuration of the natural product as (R).
authors.affiliation: University of Basel, Department of Chemistry, 4056 Basel, Switzerland.
authors.forename: Henning J
authors.initials: HJ
authors.lastname: Jessen
authors.forename: Andreas
authors.initials: A
authors.lastname: Schumacher
authors.forename: Fabian
authors.initials: F
authors.lastname: Schmid
authors.forename: Andreas
authors.initials: A
authors.lastname: Pfaltz
authors.forename: Karl
authors.initials: K
authors.lastname: Gademann
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D011728:Pyridones; C562285:torrubiellone C