title: Enantioselective total synthesis of aperidine.
abstract: An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, Suruga-ku, Shizuoka, Japan. wakimoto@mol.f.u-tokyo.ac.jp
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Wakimoto
authors.forename: Kakeru
authors.initials: K
authors.lastname: Miyata
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Ohuchi
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Haruo
authors.initials: H
authors.lastname: Nukaya
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Suwa
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D001515:Beer; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D018727:Muscarinic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D006146:Guanidines; D018727:Muscarinic Antagonists; C559565:aperidine; D012238:Rhodium