Triflic Acid-Mediated Rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: Synthesis of Methoxytropolones and Furans

Autor:	Yvonne D. Williams, Ryan P. Murelli, Christine Meck, Noushad Mohd
Jazyk:	angličtina
Rok vydání:	2013
Předmět:	Dimethyl acetylenedicarboxylate Mesylates Molecular Structure Stereochemistry Chemistry Organic Chemistry Biological activity Bridged Bicyclo Compounds Heterocyclic Tropolone Article chemistry.chemical_compound Molecule Furans Triflic acid
Popis:	Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R(2) = R(3) = CO2Me) instead form furans as the major product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f236dbaea81ef6032560fe3408623b28 https://europepmc.org/articles/PMC3909939/ Zobrazit plný text záznamu