Literature DB >> 28492076

Total Synthesis of γ-Indomycinone and Kidamycinone by Means of Two Regioselective Diels-Alder Reactions.

Thibaud Mabit1, Aymeric Siard1, Mathilde Pantin1, Doumadé Zon1, Laura Foulgoc1, Drissa Sissouma1, André Guingant1, Monique Mathé-Allainmat1, Jacques Lebreton1, François Carreaux2, Gilles Dujardin3, Sylvain Collet1.   

Abstract

An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels-Alder reactions. A first Diels-Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substituted dienes which will be involved in the second pericyclic reaction with juglone to construct the tetracyclic core of pluramycinones.

Entities:  

Year:  2017        PMID: 28492076     DOI: 10.1021/acs.joc.7b00544

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


  1 in total

1.  Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step.

Authors:  Pierre-Antoine Nocquet; Aurélie Macé; Frédéric Legros; Jacques Lebreton; Gilles Dujardin; Sylvain Collet; Arnaud Martel; Bertrand Carboni; François Carreaux
Journal:  Beilstein J Org Chem       Date:  2018-11-29       Impact factor: 2.883

  1 in total

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