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

Johanna Revol-Cavalier (1) , Valérie Bultel-Poncé (1) , Alexandre Guy (1) , Thierry Durand (1) , Camille Oger (1) , Jean-Marie Galano (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

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.

Domaines: Chimie

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⟩