Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

M. El Assal , P.A. Peixoto , R. Coffinier , T. Garnier , D. Deffieux , Karinne Miqueu (1) , Jean-Marc Sotiropoulos (1) , L. Pouységu , S. Quideau

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

A concise synthesis of two scyphostatin analogues is achieved from readily available ortho-substituted phenols. Key features include an asymmetric and biomimetic hydroxylative phenol dearomatization (HPD) reaction promoted by a chiral salen-type bis(λ5-iodane) reagent, followed by an in situ regio- and diastereocontrolled epoxidation. © 2017 American Chemical Society.

Domaines: Chimie

M. El Assal, P.A. Peixoto, R. Coffinier, T. Garnier, D. Deffieux, et al.. Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization. Journal of Organic Chemistry, 2017, 82 (22), pp.11816-11828. ⟨10.1021/acs.joc.7b02366⟩. ⟨hal-01679474⟩