Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones

Article Article scientifique Article Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones eng 2018 author Lagoutte Roman 798390 author Pastor Fernandez Miryam 875790 author Berthet Mathéo 882867 author Winssinger Nicolas 769664 6012-6021 10.1016/j.tet.2018.08.045 0040-4020 https://linkinghub.elsevier.com/retrieve/pii/S0040402018310275 The sesquiterpene lactones cover a diverse and pharmacologically important diversity space. In particular, the electrophilic α-exo-methylene-γ-butyrolactone moiety that is preponderant in this natural product family has been shown to readily engage in covalent inhibition via conjugate addition of cysteine residues in target proteins. However, the synthetic accessibility of sesquiterpenes or related probes to investigate their mode of action remains laborious. Herein, we present a rapid and scalable route to chiral bromolactones as enabling precursors in the synthesis of sesquiterpene lactones. Sesquiterpene lactones Covalent inhibitors α-exo-methylene-γ-butyrolactones Bromolactones Enantioselective synthesis Barbier coupling Dewey 540 36 Département de chimie organique 141 false 762 Groupe Winssinger Tetrahedron 74 41 2eef07d6-e5ef-48a0-9e07-3361b7464e1c Article (Published version) Restricted 1-s2.0-S0040402018310275-main.pdf 1195920 application/pdf ce88987d-b813-48ec-bd75-2c6671ebd590 Article (Accepted version) Public 141-Rapid ScalableBromolactone-Lagoutte-Tetrahedron2018.pdf 1636249 application/pdf openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones	Tetrahedron			2018	507	505

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Pastor Fernandez, Miryam