The Domestication of ortho-Quinone Methides

WJ Bai, JG David, ZG Feng, MG Weaver… - Accounts of chemical …, 2014 - ACS Publications
Conspectus An ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed
by nature for a variety of purposes. Given its extraordinary reactivity and biological …

Skipped dienes in natural product synthesis

G Petruncio, Z Shellnutt, S Elahi-Mohassel… - Natural Product …, 2021 - pubs.rsc.org
Covering: 2000–2020 The 1, 4-diene motif, also known as a skipped diene, is widespread
across various classes of natural products including alkaloids, fatty acids, terpenoids, and …

Modular Construction of Heterobiaryl Atropisomers and Axially Chiral Styrenes via All‐Carbon Tetrasubstituted VQMs

BB Gou, Y Tang, YH Lin, L Yu, QS Jian… - Angewandte Chemie …, 2022 - Wiley Online Library
Here we report a new type of chiral all‐carbon tetrasubstituted VQMs generated via chiral
phosphoric acids catalyzed nucleophilic addition of 2‐alkynylnaphthols to o‐quinone …

ortho‐Quinone Methides in Natural Product Synthesis

NJ Willis, CD Bray - Chemistry–A European Journal, 2012 - Wiley Online Library
Abstract ortho‐Quinone methides (o‐QMs) are emerging as highly useful intermediates, the
inherent reactivity of which can be used in linchpin reactions for the construction of complex …

Chiral organic contact ion pairs in metal-free catalytic asymmetric allylic substitutions

M Rueping, U Uria, MY Lin… - Journal of the American …, 2011 - ACS Publications
Chiral contact ion-pair catalysis with particular focus on metal-free processes is gaining in
interest. As a result, new perspectives are opened, and highly stereoselective …

gem-Difluoro-Masked o-Quinone Methides Generated by Photocatalytic Radical (3+3) Annulation and Their (4+1) Cycloaddition with Sulfur Ylides

S Li, L Zhou - Organic Letters, 2023 - ACS Publications
A visible light-promoted radical (3+ 3) annulation of vinyldiazo compounds and
bromodifluoromethyl alkynyl ketones for the construction of gem-difluoro-masked o-quinone …

Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation

K Gebauer, F Reuß, M Spanka, C Schneider - Organic letters, 2017 - ACS Publications
The combination of an in situ formed MnL3 complex (HL= Hacac or R (C O) CH2CO2R)
and a chiral phosphoric acid HX* allows for a fully catalytic, asymmetric synthesis of 4 H …

ortho-Quinone Methides from para-Quinones: Total Synthesis of Rubioncolin B

JP Lumb, KC Choong, D Trauner - Journal of the American …, 2008 - ACS Publications
A concise synthesis of rubioncolin B is described, which features an unprecedented
intramolecular Diels− Alder reaction involving an ortho-quinone methide and a …

A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2, 3-dihydrobenzofuran synthesis

F Zhou, Y Cheng, XP Liu, JR Chen… - Chemical …, 2019 - pubs.rsc.org
A visible light photoredox-catalyzed carbon radical-mediated strategy for in situ formation of
ortho-quinone methides from 2-vinyl phenols is described. This strategy enables a …

Meroterpenes from marine invertebrates: Structures, occurrence, and ecological implications

M Menna, C Imperatore, F D'Aniello, A Aiello - Marine Drugs, 2013 - mdpi.com
Meroterpenes are widely distributed among marine organisms; they are particularly
abundant within brown algae, but other important sources include microorganisms and …