Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A - Département de chimie Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A

Résumé

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

Domaines

Chimie organique
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Dates et versions

hal-03313908 , version 1 (07-10-2021)

Licence

Paternité - Pas d'utilisation commerciale - Pas de modification

Identifiants

Citer

Oscar Gayraud, Benjamin Laroche, Nicolas Casaretto, Bastien Nay. Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A. Organic Letters, 2021, 23, pp.5755-5760. ⟨10.1021/acs.orglett.1c01922⟩. ⟨hal-03313908⟩
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