Poly-oxygenated tricyclobutabenzenes via repeated [2 + 2] cycloaddition of benzyne and ketene silyl acetal

Journal of the American Chemical Society
Toshiyuki HamuraKeisuke Suzuki

Abstract

Described herein is a synthesis of highly functionalized tricyclobutabenzenes, a class of molecules of structural and theoretical interest. The preparation is based on the repeated [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where two types of regioselectivity enable discrimination of the functionalities on the four-membered rings. By these steps, we were able to prepare poly-oxygenated octamethoxytricyclobutabenzene and its hydrolyzed tetra-oxo derivatives. Structural study on the latter compound showed the interesting properties related to the strained four-membered ring.

References

Sep 6, 1996·The Journal of Organic Chemistry·Giovanni CerioniThomas T. Tidwell

❮ Previous
Next ❯

Citations

Jan 18, 2017·The Journal of Organic Chemistry·I N Chaithanya KiranYun He
Feb 22, 2017·Chemical Society Reviews·Jiarong ShiYang Li
Aug 26, 2016·Chemical Communications : Chem Comm·Suguru YoshidaTakamitsu Hosoya
Nov 3, 2015·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Eito Yoshioka
May 18, 2007·Angewandte Chemie·Holger Butenschön
Sep 19, 2019·Angewandte Chemie·Daniel B Werz, Akkattu T Biju
Nov 8, 2020·Chemistry : a European Journal·Kazuhiko AdachiToshiyuki Hamura
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Dec 30, 2009·Journal of the American Chemical Society·Paula Alvarez-BercedoRuben Martin
May 8, 2009·Organic Letters·Tongyu XuLiandi Wang
Jun 26, 2014·Organic Letters·Sachin Suresh BhojgudeAkkattu T Biju
Dec 31, 2016·Journal of the American Chemical Society·Jiarong ShiYang Li
Sep 29, 2020·The Journal of Organic Chemistry·Eito YoshiokaHideto Miyabe
Oct 1, 2011·Organic Letters·Mateo AlajarinRaul-Angel Orenes
Jan 28, 2020·Accounts of Chemical Research·Jia HeYang Li

❮ Previous
Next ❯

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.

© 2021 Meta ULC. All rights reserved