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2 article(s) from Carboni, Bertrand

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

Pierre-Antoine Nocquet,
Aurélie Macé,
Frédéric Legros,
Jacques Lebreton,
Gilles Dujardin,
Sylvain Collet,
Arnaud Martel,
Bertrand Carboni and
François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

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Graphical Abstract

Figure 1: N,N-Dimethyl-L-vancosamine as substructure of kidamycin and pluramycin.

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Figure 2: Glycals as relevant scaffolds for constructing aryl C-glycosidic linkage.

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Figure 3: Strategy including a ring-closing metathesis of vinyl ethers as key step for the preparation of sev...

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Scheme 1: Evans aldol reaction for the preparation of diastereomeric compounds 13a and 13b.

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Scheme 2: Alternative preparation of 13b based on a diastereoselective allylboration.

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Scheme 3: O-Vinylation-ring-closing metathesis sequence for access to 3-amino glycals.

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Scheme 4: Synthesis of key intermediate 23 for the C-3 unbranched amino glycals preparation.

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Scheme 5: Access to diastereoisomeric compounds 3 and 4 from 23.

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Supp Info

Full Research Paper

Published 29 Nov 2018

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Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

Ludovic Eberlin,
Fabien Tripoteau,
François Carreaux,
Andrew Whiting and
Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

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Scheme 1: 1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.

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Scheme 2: Lewis acid catalyst in the tandem cycloaddition [4 + 2]/allylboration sequence.

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Scheme 3: Synthesis of an advanced precursor of clerodin.

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Scheme 4: Intramolecular Diels–Alder/allylboration sequence.

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Scheme 5: Diastereoselective Diels–Alder reaction with N-phenylmaleimide and 4-phenyltriazoline-3,5-dione.

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Scheme 6: Asymmetric synthesis of a α-hydroxyalkylcyclohexane.

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Scheme 7: Tandem [4 + 2]-cycloaddition/allylboration of 3-silyloxy- and 4-alkoxy-dienyl boronates.

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Scheme 8: Metal-mediated cycloisomerization/Diels–Alder reaction/allylboration sequence.

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Scheme 9: Cobalt-catalyzed Diels–Alder/allylboration sequence.

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Scheme 10: A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.

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Scheme 11: Tandem sequence based on the Petasis borono–Mannich reaction as first key step.

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Scheme 12: One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.

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Scheme 13: Tandem Diels–Alder/cross-coupling reactions of trifluoroborates 15.

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Scheme 14: Diels–Alder/cross-coupling reactions of 16.

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Scheme 15: Metal catalyzed tandem Diels–Alder/hydrolysis reactions.

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Scheme 16: Synthesis of anti-1,5-diols 18 by triple aldehyde addition.

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Scheme 17: Catalytic enantioselective three-component hetero-[4 + 2]-cycloaddition/allylboration sequence.

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Scheme 18: Synthesis of natural products using the catalytic enantioselective HDA/allylboration sequence.

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Scheme 19: Total synthesis of a thiomarinol derivative.

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Scheme 20: Synthesis of an advanced intermediate 27 for the east fragment of palmerolide A.

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Scheme 21: Bicyclic piperidines from tandem aza-[4 + 2]-cycloaddition/allylboration.

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Scheme 22: Hydrogenolysis reactions of hydrazinopiperidines.

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Scheme 23: Tandem aza-[4 + 2]-cycloaddition/allylboration/retrosulfinyl-ene sequence.

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Scheme 24: Boronated heterodendralene 32 in [4 + 2]-cycloadditions.

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Scheme 25: Synthesis of tricyclic imides derivatives.

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Scheme 26: Synthesis of 37 via a HDA/allylboration/DA sequence.

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Scheme 27: Diels–Alder/allylboration sequence.

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Review

Published 22 Jan 2014

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