2. Academic Validation
  3. Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

  • J Org Chem. 2017 Nov 17;82(22):11816-11828. doi: 10.1021/acs.joc.7b02366.
Mourad El Assal 1,  Philippe A Peixoto 1,  Romain Coffinier 1,  Tony Garnier 1,  Denis Deffieux 1,  Karinne Miqueu 2,  Jean-Marc Sotiropoulos 2,  Laurent Pouységu 1,  Stéphane Quideau 1
Affiliations

Affiliations

  • 1 Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405 Talence Cedex, France.
  • 2 CNRS/UNIV PAU & PAYS ADOUR , Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux (IPREM, UMR 5254), Hélioparc, 2 avenue du Président Angot, 64053 Pau Cedex 09, France.
PMID: 28991470 DOI: 10.1021/acs.joc.7b02366
Abstract

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.

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