Literature DB >> 23106356

Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the Aspidosperma alkaloids (±)-limaspermidine and (±)-1-acetylaspidoalbidine.

Shen H Tan1, Martin G Banwell, Anthony C Willis, Tristan A Reekie.   

Abstract

The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].

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Year:  2012        PMID: 23106356     DOI: 10.1021/ol3026846

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


  5 in total

1.  Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine.

Authors:  Arun K Ghosh; Joshua R Born; Luke A Kassekert
Journal:  J Org Chem       Date:  2019-04-02       Impact factor: 4.354

Review 2.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors:  Beau P Pritchett; Brian M Stoltz
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

3.  Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Authors:  Beau P Pritchett; Etienne J Donckele; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-05       Impact factor: 15.336

4.  Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives.

Authors:  Kolby L White; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-08-26       Impact factor: 15.419

5.  Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.

Authors:  Kiyoun Lee; Dale L Boger
Journal:  J Am Chem Soc       Date:  2014-02-17       Impact factor: 15.419

  5 in total

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