Geometry‐Controlled Cycloaddition of<i>C</i>‐Alkoxycarbonyl Nitrones: Synthetic Studies on Nonproteinogenic Amino Acids

Tamura, Osamu

doi:10.1002/9781118778173.ch06

Methods and Applications of Cycloaddition Reactions in Organic Syntheses 2014

DOI: 10.1002/9781118778173.ch06

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Geometry‐Controlled Cycloaddition ofC‐Alkoxycarbonyl Nitrones: Synthetic Studies on Nonproteinogenic Amino Acids

Osamu Tamura

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Cited by 3 publications

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“…Thus, cycloaddition of fully functionalized allyl alcohol B with ester-substituted nitrone C would give isoxazolidine A , whose hydrogenolysis followed by intramolecular S N 2 reaction should afford the target molecule 2 . We chose cyclic nitrone 3 as a chiral and geometry-fixed nitrone corresponding to C . − Thus, the first task was the synthesis of the fully functionalized allyl alcohol corresponding to B .…”

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Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

et al. 2017

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The total synthesis of neodysiherbaine A was achieved via 1,3-dipolar cycloaddition of a chiral nitrone template with a sugar-derived allyl alcohol in the presence of MgBr·OEt. This cycloaddition constructed the C2 and C4 asymmetric centers in a single step. Then reductive cleavage, intramolecular S2 reaction of the tertiary alcohol, and oxidation of the primary alcohol afforded neodysiherbaine A.

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Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

et al. 2017

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[3+2] Route to Quaternary Oxaprolinol Derivatives as Masked Precursors of Disubstituted β³,β³‐Amino Aldehyde

et al. 2015

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Bicyclic isoxazolidines displaying one or two quaternary stereocenter(s) were formed starting from functional cyclic ketonitrones equipped with a phenyl glycinol chiral auxiliary. The products were engaged in stereocontrolled 1,3‐dipolar cycloaddition reactions with a range of electron‐rich and electron‐poor dipolarophiles. A new reductive removal of the phenyl glycinol chiral auxiliary was introduced and was shown to afford chemoselectively a quaternary isoxazolidine derivative (of oxaprolinol‐type) without cleaving the N–O isoxazolidine bond. Keeping the aldehyde function masked as a cyclic pseudo‐acetal, the liberated oxy‐amine function was shown to be available for a pseudo‐peptide coupling with various N‐protected amino acids. The isoxazolidine ring was opened by a reductive N–O bond cleavage, giving a pseudo‐dipeptide that was C‐terminated with an aldehyde function.

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Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

Tamura¹,

Ueda²,

Inada³

et al. 2015

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Geometry‐Controlled Cycloaddition ofC‐Alkoxycarbonyl Nitrones: Synthetic Studies on Nonproteinogenic Amino Acids

Cited by 3 publications

References 131 publications

Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

[3+2] Route to Quaternary Oxaprolinol Derivatives as Masked Precursors of Disubstituted β³,β³‐Amino Aldehyde

Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

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Geometry‐Controlled Cycloaddition ofC‐Alkoxycarbonyl Nitrones: Synthetic Studies on Nonproteinogenic Amino Acids

Cited by 3 publications

References 131 publications

Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template

[3+2] Route to Quaternary Oxaprolinol Derivatives as Masked Precursors of Disubstituted β3,β3‐Amino Aldehyde

Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

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Product

Resources

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[3+2] Route to Quaternary Oxaprolinol Derivatives as Masked Precursors of Disubstituted β³,β³‐Amino Aldehyde