o-Quinone Methides via Oxone-Mediated Benzofuran Oxidative Dearomatization and Their Intramolecular Cycloaddition with Carbonyl Groups: An Expeditious Construction of the Central Tetracyclic Core of Integrastatins, Epicoccolide A, and Epicocconigrone A

Organic Letters
Atul A More, Chepuri V Ramana

Abstract

The intramolecular cycloaddition of o-quinone methides (o-QMs) with a carbonyl group has been envisaged and executed successfully in the context of constructing the complex and rare [6,6,6,6]-tetracyclic core found in the integrastatins, epicoccolide A, and epicocconigrone A. These transient o-QMs were generated easily from the oxidative dearomatization of the corresponding C2-(aryl)benzofuran by employing Oxone in acetone-water at rt. The subsequent cycloaddition with the carbonyl (or conjugated olefin) present on the C2-aryl group was spontaneous.

References

Nov 7, 2003·Organic Letters·Jonathan S FootRichard J K Taylor
Aug 11, 2004·Toxicon : Official Journal of the International Society on Toxinology·M GordalizaM A Gómez-Zurita
Jul 3, 2008·Chemical Communications : Chem Comm·C V RamanaRajesh G Gonnade
Mar 20, 2010·Organic Letters·Andrew L LawrenceAmber L Thompson
Apr 17, 2010·Organic Letters·Jonathan H GeorgeRobert M Adlington
Sep 21, 2010·Chemistry : a European Journal·Thomas N SnaddonAlois Fürstner
Dec 9, 2010·Organic Letters·Todd A WenderskiThomas R R Pettus
Apr 21, 2011·Angewandte Chemie·Stéphane P Roche, John A Porco
Jun 18, 2011·Organic & Biomolecular Chemistry·Pamela M TadrossBrian M Stoltz
Sep 21, 2011·Organic Letters·Jason C GreenThomas R R Pettus
Oct 18, 2011·The Journal of Organic Chemistry·Tejas P Pathak, Matthew S Sigman
Nov 15, 2011·The Journal of Organic Chemistry·Wen-Ju BaiThomas R R Pettus
Jun 19, 2012·Chemistry : a European Journal·Nicky J Willis, Christopher D Bray
Dec 5, 2012·Angewandte Chemie·Chun-Xiang ZhuoShu-Li You
Mar 5, 2013·Chemical Reviews·Hidayat HussainIshtiaq Ahmed
Jul 11, 2013·Organic Letters·Justin T J Spence, Jonathan H George
Dec 18, 2013·Journal of Natural Products·Mustapha El AmraniPeter Proksch
May 21, 2014·Angewandte Chemie·Tue H JepsenScott A Snyder
Jun 28, 2014·Organic Letters·Liyan SongRongbiao Tong
Dec 4, 2014·Accounts of Chemical Research·Wen-Ju BaiThomas R R Pettus
Jan 1, 2012·Pure and Applied Chemistry. Chimie Pure Et Appliquée·Jason C GreenThomas R R Pettus
Sep 10, 2015·The Journal of Organic Chemistry·Anais GervaisJohn A Porco
Dec 4, 2015·Journal of the American Chemical Society·Ken-Ichi TakaoKin-Ichi Tadano

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.