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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Published inBeilstein journal of organic chemistry Vol. 14; no. 1; pp. 2949 - 2955
Main Authors Nocquet, Pierre-Antoine, Macé, Aurélie, Legros, Frédéric, Lebreton, Jacques, Dujardin, Gilles, Collet, Sylvain, Martel, Arnaud, Carboni, Bertrand, Carreaux, François
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 29.11.2018
Beilstein-Institut
Subjects
3-amino glycals
Alcohol
Antibiotics
Chemical Sciences
Chemistry
diastereoselective additions to aldehydes
Ethers
Full Research Paper
Lactic acid
Natural products
Organic chemistry
pluramycins
ring-closing metathesis
vinyl ethers
France
3-amino glycals
diastereoselective additions to aldehydes
pluramycins
vinyl ethers
ring-closing metathesis
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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PMCID: PMC6278755
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.14.274