title: Total synthesis of (-)-ardeemin.
abstract: Total synthesis of potent anti-MDR indole alkaloids (-)-ardeemin and its N-acyl analogues has been accomplished from L-tryptophan with about 2% overall yield in 20 steps. The key step depended on the newly developed three-step one-pot cascade reaction of 7 with diazoester 8 via intermolecular cyclopropanation, ring opening, and ring closure to assemble the chiral 3-substituted hexahydropyrrolo[2,3-b]indole 4a.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Novel Delivery System of Ministry of Education, West China School of Pharmacy, Chengdu 610041, PR China.
authors.forename: Bin
authors.initials: B
authors.lastname: He
authors.forename: Hao
authors.initials: H
authors.lastname: Song
authors.forename: Yu
authors.initials: Y
authors.lastname: Du
authors.forename: Yong
authors.initials: Y
authors.lastname: Qin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; C534892:ardeemin