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

Abstract : 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.
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Pierre-Antoine Nocquet, Aurélie Macé, Frédéric Legros, Jacques Lebreton, Gilles Dujardin, et al.. 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, Beilstein-Institut, 2018, 14, pp.2949-2955. ⟨10.3762/bjoc.14.274⟩. ⟨hal-01973903⟩

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