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

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

In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring-closing metathesis of vinyl ethers as key st...

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Main Authors: Pierre-Antoine Nocquet, Aurélie Macé, Frédéric Legros, Jacques Lebreton, Gilles Dujardin, Sylvain Collet, Arnaud Martel, Bertrand Carboni, François Carreaux
Format: Article
Language:English
Published: Beilstein-Institut 2018-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
3-amino glycals
diastereoselective additions to aldehydes
pluramycins
ring-closing metathesis
vinyl ethers
Online Access:https://doi.org/10.3762/bjoc.14.274
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spelling doaj-9896b24e345f48058322f68eba14ab872021-02-02T04:39:12ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-11-011412949295510.3762/bjoc.14.2741860-5397-14-274Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis stepPierre-Antoine Nocquet0Aurélie Macé1Frédéric Legros2Jacques Lebreton3Gilles Dujardin4Sylvain Collet5Arnaud Martel6Bertrand Carboni7François Carreaux8Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes, FranceUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes, FranceInstitut des Molécules et Matériaux du Mans, UMR 6283 CNRS-Université du Maine, avenue Olivier Messiaen, 72085 Cedex Le Mans, FranceChimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR 6230 CNRS-Université de Nantes, 2 chemin de la Houssinière, 44322 Cedex Nantes, FranceInstitut des Molécules et Matériaux du Mans, UMR 6283 CNRS-Université du Maine, avenue Olivier Messiaen, 72085 Cedex Le Mans, FranceChimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR 6230 CNRS-Université de Nantes, 2 chemin de la Houssinière, 44322 Cedex Nantes, FranceInstitut des Molécules et Matériaux du Mans, UMR 6283 CNRS-Université du Maine, avenue Olivier Messiaen, 72085 Cedex Le Mans, FranceUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes, FranceUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes, FranceIn this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring-closing metathesis of vinyl ethers as key step of reaction sequences developed.https://doi.org/10.3762/bjoc.14.2743-amino glycalsdiastereoselective additions to aldehydespluramycinsring-closing metathesisvinyl ethers
collection DOAJ
language English
format Article
sources DOAJ
author Pierre-Antoine Nocquet
Aurélie Macé
Frédéric Legros
Jacques Lebreton
Gilles Dujardin
Sylvain Collet
Arnaud Martel
Bertrand Carboni
François Carreaux
spellingShingle Pierre-Antoine Nocquet
Aurélie Macé
Frédéric Legros
Jacques Lebreton
Gilles Dujardin
Sylvain Collet
Arnaud Martel
Bertrand Carboni
François Carreaux
Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
Beilstein Journal of Organic Chemistry
3-amino glycals
diastereoselective additions to aldehydes
pluramycins
ring-closing metathesis
vinyl ethers
author_facet Pierre-Antoine Nocquet
Aurélie Macé
Frédéric Legros
Jacques Lebreton
Gilles Dujardin
Sylvain Collet
Arnaud Martel
Bertrand Carboni
François Carreaux
author_sort Pierre-Antoine Nocquet
title Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
title_short Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
title_full Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
title_fullStr Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
title_full_unstemmed Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
title_sort stereodivergent approach in the protected glycal synthesis of l-vancosamine, l-saccharosamine, l-daunosamine and l-ristosamine involving a ring-closing metathesis step
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2018-11-01
description In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring-closing metathesis of vinyl ethers as key step of reaction sequences developed.
topic 3-amino glycals
diastereoselective additions to aldehydes
pluramycins
ring-closing metathesis
vinyl ethers
url https://doi.org/10.3762/bjoc.14.274
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