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

Johanna Revol-Cavalier | Zendy; Valérie BultelPoncé | Zendy; Alexandre Guy | Zendy; Thierry Durand | Zendy; Camille Oger | Zendy; JeanMarie Galano | Zendy

Open Access

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

Author(s) -

Johanna Revol-Cavalier,

Valérie BultelPoncé,

Alexandre Guy,

Thierry Durand,

Camille Oger,

JeanMarie Galano

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02553

Subject(s) - intramolecular force , cyclopentane , chemistry , docosahexaenoic acid , derivative (finance) , michael reaction , prostanoid , prostaglandin , total synthesis , stereochemistry , stereoisomerism , fatty acid , polyunsaturated fatty acid , organic chemistry , biochemistry , molecule , catalysis , financial economics , economics

The total synthesis of a docosahexaenoic-acid-derived prostaglandin, 4,11- diepi -4-F 4 -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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