Literature DB >> 16248638

Stereocontrolled total synthesis of (-)-eudistomin C.

Tohru Yamashita1, Nobutaka Kawai, Hidetoshi Tokuyama, Tohru Fukuyama.   

Abstract

A stereocontrolled total synthesis of (-)-eudistomin C was accomplished in 18-step sequence with an overall yield of 7.7%. The synthesis features the diastereoselective Pictet-Spengler reaction of a tryptamine derivative and the Garner aldehyde catalyzed by Bronsted acids, and the unprecedented construction of the unusual oxathiazepine ring by intramolecular alkylation.

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Year:  2005        PMID: 16248638     DOI: 10.1021/ja055832h

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


  8 in total

1.  Total synthesis of (+)-sieboldine a: evolution of a pinacol-terminated cyclization strategy.

Authors:  Stephen M Canham; David J France; Larry E Overman
Journal:  J Org Chem       Date:  2012-06-26       Impact factor: 4.354

2.  Total synthesis of (+)-sieboldine A.

Authors:  Stephen M Canham; David J France; Larry E Overman
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

3.  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

4.  Weak Brønsted acid-thiourea co-catalysis: enantioselective, catalytic protio-Pictet-Spengler reactions.

Authors:  Rebekka S Klausen; Eric N Jacobsen
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

5.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

6.  Reactivity of 4-tert-butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with hydrazines.

Authors:  Javier Figueroa; Esther Caballero; Pilar Puebla; Fernando Tomé; Manuel Medarde
Journal:  Molecules       Date:  2006-11-30       Impact factor: 4.411

Review 7.  The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

Authors:  Renato Dalpozzo
Journal:  Molecules       Date:  2016-05-27       Impact factor: 4.411

Review 8.  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 in total

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