SAMARIUM · Samarium (II) lodide induced cyclisations leading to new steroid-like compounds

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Project objective

Samarium(II) iodide is an extremely versatile reagent in synthetic organic chemistry. Of particular interest are electron-transfer reactions to carbonyl compounds, which provide ketyls capable of undergoing inter- and intramolecular additions to unsaturated groups.Recently in the group of Prof. Reissig a novel intramolecular reaction involving aryl groups has been discovered, which afforded highly substituted hexahydronaphthalene derivatives with excellent diastereoselectivities. The research proposal deals with the corresponding samarium(II) iodide induced intramolecular reaction of ketyls derived from cyclic ketones with naphthyl substituents or related bicyclic (hetero)aryl groups.They should lead to tetracyclic products with steroid-like structure and azasteroid derivatives. Scope and limitations of these reactions will be studied as well as the features which influence the stereochemistry of the processes. An extension to enantioenriched precursor compounds is planned, which should be available by asymmetric deprotonation and subsequent alkylation, and finally afford enantioenriched products.Due to the high degree of functionalisation the products may be further transformed into a variety of products of high interest because of their potential biological activity. Thus, high product diversity may be achieved within a few steps.

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Participants

• FREIE UNIVERSITAET BERLIN · BERLINCoordinatorGermany

Links

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