An efficient synthesis of the 1-hydroxy-2-(prop-2'-enyl)9-anthrone is described. Selective nitration of anthraquinone, reduction to the corresponding amine, diazotization and treatment by sulfuric acid solution afforded the 1-hydroxy-9,10-anthraquinone in good yield as the key intermediate. Reaction with allyl bromide/K2CO3 and subsequent selective reduction accompanie...

Unsaturated epsilon-lactones bearing an alpha-arylsulfonyl or alpha-arylsulfoximinyl substituent undergo stereoselective transannular, decarboxylative Claisen rearrangement to give substituted vinylcyclopropanes.

The development of an enantioselective catalytic Claisen rearrangement1 remains an important yet elusive goal in chemical synthesis.2 With this objective in mind, we recently reported the acyl-Claisen rearrangement, a Lewis acid-catalyzed variant of the Bellus reaction3 that utilizes acid chlorides and allylic amines in the stereoselective synthesis of R,â-disubstituted-γ,δ-unsaturated carbonyl...

Unsaturated eight-membered lactones undergo decarboxylative and non-decarboxylative transannular Ireland-Claisen rearrangement reactions, to give substituted vinylcyclobutanes. A formal synthesis of (±)-grandisol is described.

A stereocontrolled synthesis of the core of eunicellin is described featuring a Claisen rearrangement and a diastereoselective organocatalytic Diels-Alder reaction as the key steps.

The underlying stereochemically complex and densely functionalized scaffold of the B-seco limonoids was synthesized employing an Ireland-Claisen rearrangement as key transformation.