Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization.
Mourad El AssalPhilippe A PeixotoRomain CoffinierTony GarnierDenis DeffieuxKarinne MiqueuJean-Marc SotiropoulosLaurent PouységuStéphane QuideauPublished in: The Journal of organic chemistry (2017)
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.