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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-03313908
Contributor : Bastien Nay Connect in order to contact the contributor
Submitted on : Thursday, October 7, 2021 - 11:05:09 AM
Last modification on : Tuesday, January 4, 2022 - 5:55:38 AM
Long-term archiving on: : Saturday, January 8, 2022 - 6:34:23 PM

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

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