Characterization of novel isobenzofuranones by DFT calculations and 2D NMR analysis

Magnetic Resonance in Chemistry : MRC
Milena G Teixeira, Elson S Alvarenga

Abstract

Phthalides are frequently found in naturally occurring substances and exhibit a broad spectrum of biological activities. In the search for compounds with insecticidal activity, phthalides have been used as versatile building blocks for the syntheses of novel potential agrochemicals. In our work, the Diels-Alder reaction between furan-2(5H)-one and cyclopentadiene was used successfully to obtain (3aR,4S,7R,7aS)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one and (3aS,4R,7S,7aR)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (2) and (3aS,4S,7R,7aR)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one and (3aR,4R,7S,7aS)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (3). The endo adduct (2) was brominated to afford (3aR,4R,5R,7R,7aS,8R)-5,8-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one and (3aS,4S,5S,7S,7aR,8S)-5,8-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one (4) and (3aS,4R,5R,6S,7S,7aR)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one and (3aR,4S,5S,6R,7R,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one (5). Following the initial analysis of the NMR spectra and the proposed two novel unforeseen products, we have decided to fully analyze the classical and non-classical...Continue Reading

References

Apr 18, 2001·Journal of Agricultural and Food Chemistry·R A Momin, M G Nair
Jul 18, 2002·Nature Reviews. Drug Discovery·Jeremy K NicholsonElaine Holmes
Aug 31, 2002·Chemistry : a European Journal·Giampaolo BaroneGiuseppe Bifulco
Apr 20, 2004·Magnetic Resonance in Chemistry : MRC·Wojciech Migda, Barbara Rys
Jul 9, 2004·Journal of Agricultural and Food Chemistry·Mitsuo MiyazawaYukio Ishikawa
Aug 19, 2004·Journal of the American Chemical Society·Andrew E TaggiFrank C Schroeder
Jul 7, 2005·Journal of Agricultural and Food Chemistry·Toshihiko TsukamotoMitsuo Miyazawa
Dec 15, 2005·Chemical Reviews·Ken-Ichi TakaoKin-ichi Tadano
Feb 3, 2007·Journal of Proteome Research·Eva Maria Lenz, Ian D Wilson
Mar 14, 2007·Journal of Ethnopharmacology·Junrong DuZhong Ming Qian
Oct 19, 2007·Angewandte Chemie·Axel G GriesbeckAngela Raabe
Feb 26, 2008·Journal of Natural Products·D Christopher Braddock, Henry S Rzepa
Mar 28, 2008·The Journal of Organic Chemistry·Stephanie M KoskowichPaul R Rablen
Mar 7, 2009·Journal of Natural Products·Bing WangKenneth M Merz
May 23, 2009·The Journal of Organic Chemistry·Steven G Smith, Jonathan M Goodman
Aug 25, 2009·Pest Management Science·Peter Jeschke
Sep 4, 2009·The Journal of Organic Chemistry·Ariel M Sarotti, Silvina C Pellegrinet
May 17, 2002·Angewandte Chemie·K C NicolaouGeorgios Vassilikogiannakis
Aug 28, 2010·Journal of the American Chemical Society·Steven G Smith, Jonathan M Goodman
Mar 29, 2011·Journal of the American Chemical Society·Giacomo SaielliAlessandro Bagno
Aug 27, 2013·Fitoterapia·Jian HuangJin-Hui Wang
Jan 25, 2014·Fitoterapia·Qian WeiYalun Su

❮ Previous
Next ❯

Citations

Jul 9, 2016·Magnetic Resonance in Chemistry : MRC·Gabriela da Costa Resende, Elson Santiago Alvarenga
Oct 30, 2016·Journal of Natural Products·Lars AndernachTill Opatz
Dec 24, 2018·Magnetic Resonance in Chemistry : MRC·Elson S AlvarengaAntonio J Demuner
Apr 27, 2019·Pest Management Science·Milena G TeixeiraDenilson F Oliveira
Jul 10, 2019·Magnetic Resonance in Chemistry : MRC·Leonid B Krivdin
Jun 26, 2020·Journal of Computational Chemistry·Jennifer Paola Hernández ManceraRicardo Vivas-Reyes
Jul 17, 2020·ChemistryOpen·Jennifer P Hernández-ManceraRicardo Vivas-Reyes
Nov 28, 2019·Magnetic Resonance in Chemistry : MRC·Bryan N S PintoElson S Alvarenga
Jan 3, 2021·Magnetic Resonance in Chemistry : MRC·Valentin A Semenov, Leonid B Krivdin
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kariny B A Torrent, Elson S Alvarenga

❮ 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.