We have optimized a synthetic approach to (±)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Brønsted acid-catalyzed pseudotransannular ring-opening of epoxide derived this cycloheptene as key step for construction 8-azabicyclo[3.2.1]octane central core. While attempting enantioselective synthesis natural product enantiopure 2-hydroxy-8-azabicyclo[3.2.1]octane we found ...

Epoxide ring-opening is a key reaction in organic chemistry. We have previously shown that B(C6F5)3, strongly Lewis acidic arylborane, exhibited high rates and unusual selectivities for catalyzing the of aliphatic epoxides with alcohols. Here we compare catalysts form B(C6H5?XFX)3 (x = 5, 4, 3, 0) determine moderately arylboranes higher regioselectivity, but slower this reaction. At temperature...

We have examined the selectivity of rat liver microsomal epoxide hydrolase (EC 3.3.2.3) toward all of the possible positional isomers of benzo-ring diol epoxides and tetrahydroepoxides of benz[a]anthracene, as well as the 1,2-diol 3,4-epoxides of triphenylene. This set includes compounds with no bay region in the vicinity of the benzo-ring, a bay-region diol group, a bay-region epoxide group, a...

Photopolymerization is the subject of a growing interest both at industrial and academic levels because it provides high reaction kinetics, low emissions volatile organic solvents in some cases, shrinking stress. This polymerization route has been largely developed using radical vinyl monomers, but to lesser extent by ring-opening (ROP). Beyond epoxides, which were first monomers polymerized ca...

Biological transformations of polyunsaturated fatty acids often lead to chemically unstable products, such as the prostaglandin endoperoxides and leukotriene A(4) epoxide of mammalian biology and the allene epoxides of plants. Here, we report on the enzymatic production of a fatty acid containing a highly strained bicyclic four-carbon ring, a moiety known previously only as a model compound for...

Immobilization of functional molecules in ordered microarrays has vast importance for many applications sensing and diagnostics. Here, the immobilization small molecule compounds protein microchannel cantilever spotting (?CS) on epoxy-terminated glass surfaces is studied via ring-opening epoxides by thiol, amine, azide, with purpose creating microscale patterns applications. For this, carrying ...

Fullerene epoxides, C₆₀O(n), having epoxide groups directly attached to the fullerene cage, constitute an interesting class of fullerene derivatives. In particular, the chemical transformations of fullerene epoxides are expected to play an important role in the development of functionalized fullerenes. This is because such transformations can readily afford a variety of mono- or polyfunctionali...

Four benzo-ring epoxides of the environmental carcinogen benzo(a)pyrene (BP) were tested for mutagenic and cytotoxic activity in 3 strains of Salmonella typhimurium (TA1538, TA98, and TA100) and in Chinese hamster V79 cells. Although very unstable in aqueous solution, 7beta,8alpha-dihydroxy-0beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (diol epoxide 1), with the 7-hydroxyl group on the s...