Work

Total Synthesis of Ectocarpin A

Year: 2025

Type: article

Abstract: A total enantioselective synthesis of ectocarpin A, an oxylipin identified through the first hydroperoxide bicyclase activity of CYP5164A3 in brown algae, has been successfully completed in 12 steps starting from tetrahydro‐1H‐cyclopentafuranone. Key transformations include the creation of the chiral tetrahydro‐1H‐cyclopentafuranone, a diastereoselective epoxidation, an enzymatic desymmetrization of a 1,4‐diol, an epimerization, and both Wittig and Julia‐Kocienski olefinations to build the carbon framework of ectocarpin A.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500381

Authors: Alexandre Guy, Thierry Durand, Camille Oger

Institutions: École Nationale Supérieure de Chimie de Montpellier, Centre National de la Recherche Scientifique, Université de Montpellier, Institut des Biomolécules Max Mousseron

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funder: Centre National de la Recherche Scientifique