Literature DB >> 15549833

Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.

Guangrong Zheng1, Linda P Dwoskin, Peter A Crooks.   

Abstract

Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

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Year:  2004        PMID： 15549833      PMCID： PMC3597091          DOI： 10.1021/jo048848j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  A highly stereoselective asymmetric synthesis of (--)-lobeline and (--)-sedamine.

Authors:  François-Xavier Felpin; Jacques Lebreton
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

Review 2.  A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse.

Authors:  Linda P Dwoskin; Peter A Crooks
Journal:  Biochem Pharmacol       Date:  2002-01-15       Impact factor: 5.858

3.  Lobeline: structure-affinity investigation of nicotinic acetylcholinergic receptor binding.

Authors:  D Flammia; M Dukat; M I Damaj; B Martin; R A Glennon
Journal:  J Med Chem       Date:  1999-09-09       Impact factor: 7.446

4.  Lobeline and structurally simplified analogs exhibit differential agonist activity and sensitivity to antagonist blockade when compared to nicotine.

Authors:  A V Terry; R Williamson; M Gattu; J W Beach; C R McCurdy; J A Sparks; J R Pauly
Journal:  Neuropharmacology       Date:  1998       Impact factor: 5.250

5.  Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters.

Authors:  Dennis K Miller; Peter A Crooks; Guangrong Zheng; Vladimir P Grinevich; Seth D Norrholm; Linda P Dwoskin
Journal:  J Pharmacol Exp Ther       Date:  2004-04-30       Impact factor: 4.030

6.  Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.

Authors:  Marco Angoli; Alessio Barilli; Giordano Lesma; Daniele Passarella; Sergio Riva; Alessandra Silvani; Bruno Danieli
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354
  6 in total
  8 in total

1.  Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids.

Authors:  Shyam Krishnan; Jeffrey T Bagdanoff; David C Ebner; Yeeman K Ramtohul; Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

Review 2.  Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: potential pharmacotherapies for the treatment of psychostimulant abuse.

Authors:  Peter A Crooks; Guangrong Zheng; Ashish P Vartak; John P Culver; Fang Zheng; David B Horton; Linda P Dwoskin
Journal:  Curr Top Med Chem       Date:  2011       Impact factor: 3.295

3.  Synthesis of Lobeline, Lobelane and their Analogues. A Review.

Authors:  Guangrong Zheng; Peter A Crooks
Journal:  Org Prep Proced Int       Date:  2015-08-17       Impact factor: 1.628

4.  Lobelane analogues as novel ligands for the vesicular monoamine transporter-2.

Authors:  Guangrong Zheng; Linda P Dwoskin; Agripina G Deaciuc; Jun Zhu; Marlon D Jones; Peter A Crooks
Journal:  Bioorg Med Chem       Date:  2005-06-02       Impact factor: 3.641

5.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

6.  Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.

Authors:  Guangrong Zheng; Linda P Dwoskin; Agripina G Deaciuc; Seth D Norrholm; Peter A Crooks
Journal:  J Med Chem       Date:  2005-08-25       Impact factor: 7.446

7.  Lobeline esters as novel ligands for neuronal nicotinic acetylcholine receptors and neurotransmitter transporters.

Authors:  Marhaba Hojahmat; David B Horton; Seth D Norrholm; Dennis K Miller; Vladimir P Grinevich; Agripina Gabriela Deaciuc; Linda P Dwoskin; Peter A Crooks
Journal:  Bioorg Med Chem       Date:  2009-12-06       Impact factor: 3.641

8.  Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Authors:  Anirudra Paul; Jae Hyun Kim; Scott D Daniel; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-17       Impact factor: 15.336
  8 in total

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