PMID: 11674459Oct 25, 2001Paper

Improved Syntheses and Some Selective Transformations of 2,2,4,4-Tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones

The Journal of Organic Chemistry
Stefan SendelbachBaldur Föhlisch


The methyl- and alkenyl-substituted furans 1b-h react with pentachloroacetone (2) and sodium 2,2,2-trifluoroethoxide solution to form the title compounds 3b-h in good yield. With the furans 1i-m bearing an oxygen or a sulfur heteroatom in the side chain, moderate yields are obtained. Dechlorination of the [4+3] cycloadducts 3 with the Zn-Cu couple leads to the corresponding oxabicyclic ketones 4. On catalytic hydrogenation of the tetrachlorooxabicyclooctenones 3a-c hydrogenolysis of the exo-carbon-chlorine bonds occurs, leading to the endo-2,endo-4-dichloro-8-oxabicyclooctan-3-ones 8a-c. With lithium aluminum hydride and Grignard reagents, 8a and 3a form the endo-3-alcohols 12a-c and 13, respectively, the latter with uncertain configuration at C-3, in a highly stereoselective manner. The ether bridge in the dechlorinated oxabicyclooctenones 4b, 4f, and 4g can be cleaved by means of trimethylsilyl triflate/triethylamine to produce the tropones 5b, 5f, and 5g. Hydrogenation of 1,5-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (4c), followed by Wolff-Kishner reduction, affords 1,5-dimethyl-8-oxabicyclo[3.2.1]octane (7). m-Chloroperbenzoic acid epoxidizes the alkenyl side chain of the tetrachlorinated oxabicycles 3d, 3e, 3g, and 3h in...Continue Reading


Jan 1, 1992·Archiv der Pharmazie·F Eiden, A Kainz
Dec 1, 1964·Tetrahedron·M A GianturcoV Flanagan
Aug 1, 1966·The Journal of Organic Chemistry·H O HouseC D Slater

❮ Previous
Next ❯


Nov 11, 2010·Chemical Communications : Chem Comm·Michael Harmata
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Baldur Föhlisch, Stefan Reiner
Nov 6, 2018·Chemical Society Reviews·Zengsheng YinPauline Chiu
Oct 9, 2007·Chemistry : a European Journal·M Carmen CarreñoM Jesús Sanz-Cuesta
Aug 28, 2018·European Journal of Organic Chemistry·Samantha M GibsonTom D Sheppard
Oct 12, 2010·Organic Letters·Fangmiao YuHongbin Zhai
Sep 27, 2003·The Journal of Organic Chemistry·Richard S GraingerJonathan W Steed
Jun 8, 2001·Journal of the American Chemical Society·K Lee, J K Cha
Jul 18, 2001·Journal of the American Chemical Society·J C Lee, J K Cha

❮ Previous
Next ❯

Trending Feeds


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 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.


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.

© 2022 Meta ULC. All rights reserved