Literature DB >> 19236094

Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine.

David B C Martin1, Christopher D Vanderwal.   

Abstract

An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine from tryptamine and pyridine.

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Year:  2009        PMID： 19236094     DOI： 10.1021/ja900640v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  A synthesis of alsmaphorazine B demonstrates the chemical feasibility of a new biogenetic hypothesis.

Authors:  Allen Y Hong; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2015-06-04       Impact factor: 15.419

Review 2.  Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors:  Jeffrey S Cannon; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

3.  A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family of Alstonia Alkaloids.

Authors:  Allen Y Hong; Christopher D Vanderwal
Journal:  Tetrahedron       Date:  2016-11-03       Impact factor: 2.457

4.  The Intramolecular Diels-Alder Reaction of Tryptamine-Derived Zincke Aldehydes Is a Stepwise Process.

Authors:  Hung V Pham; David B C Martin; Christopher D Vanderwal; K N Houk
Journal:  Chem Sci       Date:  2012-02-02       Impact factor: 9.825

Review 5.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

6.  Brønsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the Strychnos alkaloids.

Authors:  Rahul V Edwankar; Chitra R Edwankar; Ojas A Namjoshi; Jeffrey R Deschamps; James M Cook
Journal:  J Nat Prod       Date:  2012-01-18       Impact factor: 4.050

7.  Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines.

Authors:  Jesse Kidd; Kristen Maiden; Jeremy B Morgan
Journal:  Tetrahedron       Date:  2016-06-30       Impact factor: 2.457

8.  Photocatalytic Indole Diels-Alder Cycloadditions Mediated by Heterogeneous Platinum-Modified Titanium Dioxide.

Authors:  Spencer P Pitre; Juan C Scaiano; Tehshik P Yoon
Journal:  ACS Catal       Date:  2017-08-11       Impact factor: 13.084

9.  Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets.

Authors:  Lorenz E Löffler; Conny Wirtz; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-28       Impact factor: 15.336

10.  Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives.

Authors:  Lele Wang; Huabin Han; Lijie Gu; Wenjing Zhang; Junwei Zhao; Qilin Wang
Journal:  Chem Sci       Date:  2021-11-09       Impact factor: 9.825
  10 in total

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