Total synthesis of resolvin D3

Ogawa, Narihito; Katagiri, Kyosuke; Haimoto, Yosuke; Kobayashi, Yuichi

doi:10.1039/d2ob00750a

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00750a

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Total synthesis of resolvin D3

Narihito Ogawa¹,

Kyosuke Katagiri²,

Yosuke Haimoto³

et al.

Abstract: Resolvin D3 was synthesized by the Suzuki–Miyaura cross-coupling reaction of C1–C8 borane with C9–C22 iodoolefin as the key reaction. The latter intermediate was obtained by the sequential Wittig reactions of...

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2024

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References 22 publications

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Stereoselective Synthesis of Volicitin and 9-D 1-Volicitin

Ogawa,

Mamada,

Niwa

et al. 2024

Synlett

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The synthesis of volicitin involved the condensation of l-(+)-glutamine with 17(S)-hydroxylinolenoic acid, derived from a Wittig reaction between the C10–C18 phosphonium salt and the C1–C9 aldehyde. The phosphonium salt was prepared through the alkynylation of a (Z)-allylic phosphate with an alkyne derived from (2S)-but-3-yn-2-ol. The deuterated aldehyde was derived with a 96% deuteration ratio by reduction of the C1–C9 methyl ester with NaBD4, followed by oxidation. Subsequently, 9-D 1-volicitin was synthesized from the monodeuterated aldehyde by using the Wittig reaction and condensation with l-(+)-glutamine.

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Stereoselective Synthesis of Volicitin and 9-D 1-Volicitin

Ogawa,

Mamada,

Niwa

et al. 2024

Synlett

Self Cite

View full text Add to dashboard Cite

show abstract

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Total synthesis of resolvin D3

Abstract: Resolvin D3 was synthesized by the Suzuki–Miyaura cross-coupling reaction of C1–C8 borane with C9–C22 iodoolefin as the key reaction. The latter intermediate was obtained by the sequential Wittig reactions of...

Cited by 1 publication

References 22 publications

Stereoselective Synthesis of Volicitin and 9-D 1-Volicitin

Stereoselective Synthesis of Volicitin and 9-D 1-Volicitin

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