Total Synthesis of a Docosahexaenoic Acid Prostanoid Using an Intramolecular Organocatalytic Michael Reaction of a Formyl-Enal Derivative

The total synthesis of a docosahexaenoic-acid-derived prostaglandin, 4,11-diepi-4-F4t-neuroprostane, featuring a complex lateral chain was achieved for the first time. A novel prostaglandin cyclopentane skeleton obtained via an intramolecular highly selective organocatalytic Michael sequence of a formyl-enal derivative allowed the desired and exclusive thermodynamic trans configuration of the lipidic lateral chains.

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Chimie

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Rev ol-Cavalier et al Org Lett, 2020, 22, 7455-7459_HAL.pdf (1.17 Mo)

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https://hal.science/hal-03026182

Soumis le : jeudi 3 juin 2021-16:02:23

Dernière modification le : mardi 23 avril 2024-09:49:13

Archivage à long terme le : samedi 4 septembre 2021-19:03:46

Dates et versions

hal-03026182 , version 1 (03-06-2021)

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HAL Id : hal-03026182 , version 1
DOI : 10.1021/acs.orglett.0c02553

Citer

Johanna Revol-Cavalier, Valérie Bultel-Poncé, Alexandre Guy, Thierry Durand, Camille Oger, et al.. Total Synthesis of a Docosahexaenoic Acid Prostanoid Using an Intramolecular Organocatalytic Michael Reaction of a Formyl-Enal Derivative. Organic Letters, 2020, 22 (19), pp.7455-7459. ⟨10.1021/acs.orglett.0c02553⟩. ⟨hal-03026182⟩

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