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- W2081439032 abstract "We present the synthesis of new steroid analogues via samarium diiodide mediated intramolecular ketyl–aryl coupling reactions of γ-naphthyl-substituted 1,3-diones. From previous experiments with γ-naphthyl monoketones high stereoselectivities with the ‘unnatural’ cis/cis annulation of rings B/C/D were expected. Surprisingly, we observed the formation of two diastereomers with cis- and trans-fused rings B and C of the tetracyclic skeleton. The diastereoselectivity proved to be strongly dependent on the amount of the proton source employed in the reaction. A rationale for this unexpected behaviour is discussed. In addition, we observed a smooth aluminium chloride induced cyclisation of one of the γ-naphthyl-substituted 1,3-diones to furnish an equilenine precursor. Another cyclisation product was converted by Grob-fragmentation into a naphthannulated cyclononane derivative." @default.
- W2081439032 created "2016-06-24" @default.
- W2081439032 creator A5047290189 @default.
- W2081439032 creator A5081413658 @default.
- W2081439032 date "2010-06-01" @default.
- W2081439032 modified "2023-10-17" @default.
- W2081439032 title "Synthesis of new steroid analogues by samarium diiodide induced cyclisations of γ-naphthyl 1,3-diones" @default.
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- W2081439032 doi "https://doi.org/10.1016/j.tetasy.2010.04.036" @default.
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