title: De Novo Asymmetric Synthesis of (+)-Monanchorin.
abstract: A de novo asymmetric total synthesis of the guanidine alkaloid natural product (+)-monanchorin has been achieved in nine steps from the commodity chemicals furan and caproic acid. The asymmetry of the route was introduced by a Noyori reduction of an acylfuran. In addition, this route relies upon an Achmatowicz rearrangement, a diastereoselective palladium catalyzed glycosylation, reductive amination, and an acid catalyzed bicyclic guanidine mixed acetal formation.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Yuzhi
authors.initials: Y
authors.lastname: Ma
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000470:Alkaloids; D000478:Alkylation; D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000737:chemistry; D006031:Glycosylation; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D006146:Guanidines; C488575:monanchorin; D010165:Palladium; C039281:furan