Literature DB >> 10814407

An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization.

M Kawahara1, A Nishida, M Nakagawa.   

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.

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Year:  2000        PMID： 10814407     DOI： 10.1021/ol005513p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

3.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

4.  Synthesis of the Alzheimer drug Posiphen into its primary metabolic products (+)-N1-norPosiphen, (+)-N8-norPosiphen and (+)-N1, N8-bisnorPosiphen, their inhibition of amyloid precursor protein, α-Synuclein synthesis, interleukin-1β release, and cholinergic action.

Authors:  Qian-Sheng Yu; Marcella Reale; Mohammad A Kamal; Harold W Holloway; Weiming Luo; Kumar Sambamurti; Balmiki Ray; Debomoy K Lahiri; Jack T Rogers; Nigel H Greig
Journal:  Antiinflamm Antiallergy Agents Med Chem       Date:  2013

5.  Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles.

Authors:  Xiao Zhang; Wen-Bo Liu; Hang-Fei Tu; Shu-Li You
Journal:  Chem Sci       Date:  2015-06-08       Impact factor: 9.825

6.  1-Alkyl-3-alkylindolin-2-imine hydrochlorides as useful building blocks in the copper-catalyzed synthesis of polycyclic indoline scaffolds.

Authors:  Can Liu; Haijun Yang; Changjin Zhu; Hua Fu
Journal:  RSC Adv       Date:  2019-03-14       Impact factor: 3.361
  6 in total

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