Literature DB >> 16050731

New concise total synthesis of (+)-lentiginosine and some structural analogues.

Francesca Cardona1, Guillermo Moreno, Francesco Guarna, Pierre Vogel, Catherine Schuetz, Pedro Merino, Andrea Goti.   

Abstract

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

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Year:  2005        PMID: 16050731     DOI: 10.1021/jo0509408

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


  7 in total

1.  Synthesis of bis-Phosphate Iminoaltritol Enantiomers and Structural Characterization with Adenine Phosphoribosyltransferase.

Authors:  Lawrence D Harris; Rajesh K Harijan; Rodrigo G Ducati; Gary B Evans; Brett M Hirsch; Vern L Schramm
Journal:  ACS Chem Biol       Date:  2017-12-14       Impact factor: 5.100

Review 2.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

3.  Enantioselective synthesis of polyhydroxyindolizidinone and quinolizidinone derivatives from a common precursor.

Authors:  Nemai Saha; Shital K Chattopadhyay
Journal:  Beilstein J Org Chem       Date:  2014-12-22       Impact factor: 2.883

4.  Synthesis of a new chiral pyrrolidine.

Authors:  Mari Fe Flores; Marta G Núñez; Rosalina F Moro; Narciso M Garrido; Isidro S Marcos; Enrique F Iglesias; Pilar García; David Díez
Journal:  Molecules       Date:  2010-03-09       Impact factor: 4.411

5.  An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating.

Authors:  Elena Petricci; Simone Zurzolo; Camilla Matassini; Samuele Maramai; Francesca Cardona; Andrea Goti; Maurizio Taddei
Journal:  Molecules       Date:  2022-07-25       Impact factor: 4.927

6.  Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones.

Authors:  Marco Bonanni; Marco Marradi; Francesca Cardona; Stefano Cicchi; Andrea Goti
Journal:  Beilstein J Org Chem       Date:  2007-12-12       Impact factor: 2.883

7.  An efficient synthesis of aldohexose-derived piperidine nitrones: precursors of piperidine iminosugars.

Authors:  Hui Zhao; Wen-Bo Zhao; Jian-She Zhu; Yue-Mei Jia; Chu-Yi Yu
Journal:  Molecules       Date:  2013-05-21       Impact factor: 4.411

  7 in total

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