Synthesis of cyclopropyl-substituted furans by brønsted Acid promoted cascade reactions

Angewandte Chemie
J Stephen ClarkLouis J Farrugia

Abstract

Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron-deficient ynenones to deliver products featuring a 2,3,5-trisubstituted furan bearing a fused cyclopropyl substituent at the 5-position. Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid-catalyzed reaction.

References

Mar 4, 2000·Bioorganic & Medicinal Chemistry Letters·M HögbergH Zhang
Apr 10, 2003·Chemical Reviews·Hélène LebelAndré B Charette
Apr 10, 2003·Chemical Reviews·Michał Fedoryński
Apr 10, 2003·Chemical Reviews·Ludger A WessjohannThies Thiemann
Dec 31, 2004·Organic Letters·Peter Wipf, Jingbo Xiao
Mar 25, 2005·The Journal of Organic Chemistry·Charles P Casey, Neil A Strotman
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Jul 11, 2008·Chemical Reviews·Zigang LiChuan He
Jan 22, 2009·Journal of the American Chemical Society·Karen S MacMillanDale L Boger
Feb 10, 2010·Proceedings of the National Academy of Sciences of the United States of America·Timothy J Donohoe, John F Bower
Dec 7, 2010·Journal of the American Chemical Society·Łukasz AlbrechtKarl Anker Jørgensen
Jan 13, 2011·Organic & Biomolecular Chemistry·Jingyu YangYanzhong Li
Mar 12, 2011·Chemical Reviews·A CormaMaria J Sabater
May 28, 2011·Organic Letters·Alicia Boto, Iván Romero-Estudillo
Oct 26, 2012·Angewandte Chemie·J Stephen ClarkYves Danoy
Jul 12, 2013·Chemistry : a European Journal·Sven P FritzVarinder K Aggarwal
Aug 21, 2013·Journal of the American Chemical Society·Ying XiaJianbo Wang

❮ Previous
Next ❯

Citations

Jul 23, 2015·The Journal of Organic Chemistry·Prabhakararao Tharra, Beeraiah Baire
Jul 30, 2015·The Journal of Organic Chemistry·Ying XiaJianbo Wang
Jun 28, 2017·Organic Letters·Chao XuJ Stephen Clark
Jun 24, 2017·Organic & Biomolecular Chemistry·Prabhakararao Tharra, Beeraiah Baire
May 16, 2018·Organic & Biomolecular Chemistry·Verena KlausJ Stephen Clark
Oct 7, 2016·Chemical Communications : Chem Comm·Prabhakararao Tharra, Beeraiah Baire
Dec 29, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yue YuHua Cao
Jan 21, 2020·Chemical Society Reviews·Dong ZhuShifa Zhu
Sep 19, 2019·The Journal of Organic Chemistry·Mengxue LiKegong Ji

❮ 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.