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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Bibliographic Details
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
Description
Summary: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.
ISSN:1860-5397

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