The first total synthesis of (+)-cytosporolide A was achieved by a biomimetic hetero-Diels-Alder reaction of (-)-fuscoatrol A with o-quinone methide generated from (+)-CJ-12,373. The dienophile, highly oxygenated caryophyllene sesquiterpenoid (-)-fuscoatrol A, was synthesized from the synthetic intermediate in our previous total synthesis of (+)-pestalotiopsin A. The o-quinone methide precursor...

A unified synthetic strategy toward caged Garcinia natural products has been designed and implemented. Central to the strategy is a tandem Claisen/Diels-Alder/Claisen rearrangement of a suitably substituted xanthone precursor to form forbesione (1a). Serving as a template, forbesione is then used to deliver representative members of this family, including desoxygaudichaudione A (4), desoxymorel...

The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically gener...

Key words (±)-talatisamine - Diels–Alder reaction [2+2] photo-cycloaddition Lemieux–Johnson oxidation retro-aldol–aldol Wagner–Meerwein rearrangement aza-Prins

Tetrahydroquinoline (1), prepared by a traditional synthetic method, the imino Diels-Alder reaction, was biotransformed by Mortierella isabelina to afford a new compound, 2, characterized by spectroscopic methods.

Strongly electron-deficient dendralenes prepared in 3 steps from methyl propiolate undergo smooth diene-transmissive Diels–Alder reactions with strongly dienophiles.

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 Diels–Alder (DA) reaction is regarded as quite a useful strategy in organic and macromolecular syntheses.

Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1,3-butadienes (2a,b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examine...

The Diels-Alder (DA) reactions of isoprene with vinylborane, dimethylvinylborane and dichlorovinylborane have been studied using density functional theory and the quantum theory of atoms in molecules. We evaluated the topological properties of the transition structures (TSs) and the evolution of such properties along the reaction paths. In accordance with previous studies, our results indicate ...