Total Synthesis and Structural Revision of Chaetoviridins A

Mehdi Makrerougras , Romain Coffinier , Samuel Oger , Arnaud Chevalier (1) , Cyrille Sabot (2) , Xavier Franck (2)

1 Lab-STICC_UBO_MOM_MF
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Domaines: Chimie

Mehdi Makrerougras, Romain Coffinier, Samuel Oger, Arnaud Chevalier, Cyrille Sabot, et al.. Total Synthesis and Structural Revision of Chaetoviridins A. Organic Letters, 2017, 19 (15), pp.4146-4149. ⟨10.1021/acs.orglett.7b02053⟩. ⟨hal-02046297⟩