Nina Toelle

• University of Vienna

Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives α,β-unsaturated esters, which coupled with a xanthate elimination yields α,β,γ,δ-unsaturated ester...

When subjected to the conditions of a Semmler-Wolff/Schroeter aromatization, the oximes of 4-benzyl-substituted tetralones undergo an electrophilic aromatic substitution reaction to form tetracyclic frameworks.

A domino process consisting of an amidation, spirocyclization, and formation of an iminium ion and electrophilic aromatic substitution of a phenylethylamine and a ketoester leads to the spirocyclic skeleton of (+)-erysotramidine, which can be further transformed into the natural alkaloid.

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A Lewis acid catalyzed domino–amidation–spirocyclization reaction is described which provides the spirocyclic core of the erythrina and B-homoerythrina alkaloids, forming three bonds in one process.

The synthesis of cephalotaxine- and cephalotaxine amide analogues 14a–c and 16a–c as well as of the deoxyharringtonine analogues 5a,b was performed employing a trimethylaluminium-mediated domino reaction of 9a–c and 8 to give the spirocyclic compounds 7a–c, which was followed by a palladium catalyzed α-arylation.Graphical abstract

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