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Total Synthesis and Structural Revision of Chaetoviridins A

Mehdi Makrerougras Romain Coffinier Samuel Oger Arnaud Chevalier 1 Cyrille Sabot 2 Xavier Franck 2
Lab-STICC - Laboratoire des sciences et techniques de l'information, de la communication et de la connaissance, IBNM - Institut Brestois du Numérique et des Mathématiques
Abstract : The first synthesis of the proposed structures of chaetoviridins A 1–4 has been achieved in 10 steps by controlling the syn- or anti-aldol side chain. The angular lactone has been regioselectively introduced by condensation of a chiral dioxin-4-one to cazisochromene. Comparison of the NMR and circular dichroism data of the synthesized and reported natural products led to the complete reassignment and renaming of the chaetoviridins.
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Submitted on : Friday, February 22, 2019 - 3:40:09 PM
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Mehdi Makrerougras, Romain Coffinier, Samuel Oger, Arnaud Chevalier, Cyrille Sabot, et al.. Total Synthesis and Structural Revision of Chaetoviridins A. Organic Letters, American Chemical Society, 2017, 19 (15), pp.4146-4149. ⟨10.1021/acs.orglett.7b02053⟩. ⟨hal-02046297⟩



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