Literature DB >> 18257582

Catalytic asymmetric total synthesis of (+)-yohimbine.

Dustin J Mergott1, Stephan J Zuend, Eric N Jacobsen.   

Abstract

The total synthesis of (+)-yohimbine was achieved in 11 steps and 14% overall yield. The absolute configuration was established through a highly enantioselective thiourea-catalyzed acyl-Pictet-Spengler reaction, and the remaining 4 stereocenters were set simultaneously in a substrate-controlled intramolecular Diels-Alder reaction.

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Year:  2008        PMID： 18257582     DOI： 10.1021/ol702781q

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


  11 in total

1.  Enantioselective Syntheses of (-)-Alloyohimbane and (-)-Yohimbane by an Efficient Enzymatic Desymmetrization Process.

Authors:  Arun K Ghosh; Anindya Sarkar
Journal:  European J Org Chem       Date:  2016-11-28

2.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

3.  Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.

Authors:  Steven Gunawan; Nathan Bedard; Christopher Foley; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2021-03-17       Impact factor: 2.415

4.  Enantioselective Syntheses of Yohimbine Alkaloids: Proving Grounds for New Catalytic Transformations.

Authors:  Eric R Miller; Karl A Scheidt
Journal:  Synthesis (Stuttg)       Date:  2021-11-02       Impact factor: 2.969

Review 5.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

6.  Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels-Alder reactions.

Authors:  Stefan Bräse; Nicole Volz; Franziska Gläser; Martin Nieger
Journal:  Beilstein J Org Chem       Date:  2012-08-28       Impact factor: 2.883

Review 7.  Application of the Asymmetric Pictet-Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Masumeh Malmir
Journal:  Molecules       Date:  2018-04-18       Impact factor: 4.411

8.  Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II.

Authors:  Yong-Hai Yuan; Xue Han; Fu-Ping Zhu; Jin-Miao Tian; Fu-Min Zhang; Xiao-Ming Zhang; Yong-Qiang Tu; Shao-Hua Wang; Xiang Guo
Journal:  Nat Commun       Date:  2019-07-29       Impact factor: 14.919

9.  Asymmetric Redox-Annulation of Cyclic Amines.

Authors:  YoungKu Kang; Weijie Chen; Martin Breugst; Daniel Seidel
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

10.  Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet-Spengler Reactions.

Authors:  Elisabeth Eger; Adam Simon; Mahima Sharma; Song Yang; Willem B Breukelaar; Gideon Grogan; K N Houk; Wolfgang Kroutil
Journal:  J Am Chem Soc       Date:  2020-01-07       Impact factor: 15.419
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