This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF(3)-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that...

We recently described a remarkable acid-catalyzed isomerization of bicyclic alkenes Ia and Ib to the betweenanenes IIa and IIb. ’ This finding suggested that certain larger ring betweenanenes might possess unusual stability relative to double bond isomers and might thus be derivable from readily available bicyclic compounds via equilibrating processes. In this report we describe several attempt...

Enantioselective organocatalytic Michael addition reactions of 1-acetylcyclohexene, 1-acetylcyclopentene and 1-acetylcyclobutene to nitroolefins have been developed. This is the first report where an α-branched enone has been activated by an amine catalyst for the asymmetric Michael addition reaction to an electrophile. The Michael products have also been cyclized to bicyclic compounds.

Bicyclic guanidines have physical, electronic and chemical properties that differentiate them from their acyclic counterparts, with many of these characteristics directly imposed by the rigid framework. These distinctive features have led to this class of molecule finding practical applications in many areas of chemistry, including organocatalysis and as ligands in coordination compounds. In ad...

Two new bicyclic acylphloroglucinol derivatives, hypercalyxone A (1-[5,7-dihydroxy-2-methyl-3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-propan-1-one, 1) and B (1-[5,7-dihydroxy-2-methyl-3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-butan-1-one, 2), have been isolated from the petroleum ether extract of the aerial parts of Hypericum amblycaly...