title: An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization.
abstract: [reaction: see text] A new and efficient synthetic route to physostigmine is described. Corey-Kim reagent reacted with tryptamine or tryptophan carbamates to give 3a-(methylthiomethyl)hexahydropyrrolo[2,3-b]indole skeletons. Formal total synthesis of racemic and chiral physostigmine was accomplished in excellent overall yields, in short steps.
authors.affiliation: Faculty of Pharmaceutical Sciences, Chiba University, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Kawahara
authors.forename: A
authors.initials: A
authors.lastname: Nishida
authors.forename: M
authors.initials: M
authors.lastname: Nakagawa
mesh_terms: D000478:Alkylation; D055095:Optics and Photonics; D010830:Physostigmine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D014364:Tryptophan; D010830:Physostigmine