3 years ago

Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization
Karinne Miqueu, Tony Garnier, Romain Coffinier, Jean-Marc Sotiropoulos, Mourad El Assal, Denis Deffieux, Laurent Pouységu, Philippe A. Peixoto, Stéphane Quideau
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02366

DOI: 10.1021/acs.joc.7b02366

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