Site-selective oxidative dearomatization of phenols and naphthols into ortho-quinols or epoxy ortho-quinols using oxone as the source of dimethyldioxirane

"This is the peer reviewed version of the following article: Advanced Synthesis and Catalysis 361.19 (2019): 4468-4473, which has been published in final form at https://doi.org/10.1002/adsc.201900660. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions"A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key stepThe authors thank Ministerio de Economía y Competitividad (Grant CTQ2017-83309-P) for financial suppor

Asymmetric Synthesis and Chiroptical Properties of Enantiopure Helical Ferrocenes

An enantiopure helical ferrocene (Rp)-5 with five ortho-condensed aromatic rings was synthesized using a PtCl2catalyzed cycloisomerization of planar-chiral 2-ethynyl-1-(4-phenanthrenyl)ferrocene (Rp)-6f, prepared in 3 steps from known enantiopure sulfinyl ferrocenyl boronic acid (SS,Sp)-7, as the source of planar chirality. This pentacyclic helical ferrocene showed a very high optical rotation value and strong CD signalsWe thank Ministerio de Economía y Competitividad (Grant CTQ2017‐83309‐P) for financial suppor

Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties

Angular tetracyclic p-peroxyquinols, p-quinols and a pentacyclic double peroxide, showing anticancer properties, were Selective oxidative dearomatization of angular tetracyclic phenols by controlled irradiation under air: synthesis of an angucyclinone‐type double peroxide with anticancer properties María J. Cabrera-Afonso,a Silvia R. Lucena,b Ángeles Juarranz,b Antonio Urbano,*a,c M. Carmen Carreño*a,c aDepartamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Cantoblanco, 28049-Madrid, Spain. bDepartamento de Biología, UAM, Cantoblanco, 28049-Madrid, Spain. cInstitute for Advanced Research in Chemical Sciences (IAdChem), UAM, Cantoblanco, 28049-Madrid, Spain. Supporting Information Placeholder synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizerWe thank MINECO (Grants CTQ2017-83309-P, CTQ2014-53894R and FIS PI15/00974) for financial suppor

Síntesis y reacciones de Diels-Alder asimétricas de (S)-p-tolilsulfinilquinonas

Tesis doctoral inédita leida en la Universdidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química. Fecha de lectura: 14-10-199