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  • Title: Stereoselective formation of tri- and tetracycles by samarium diiodide-induced cyclizations of naphthyl-substituted ketones.
    Author: Berndt M, Hlobilová I, Reissig HU.
    Journal: Org Lett; 2004 Mar 18; 6(6):957-60. PubMed ID: 15012074.
    Abstract:
    [reaction: see text] Samarium diiodide promotes smooth reductive cyclizations of gamma-naphthyl-substituted ketones to afford tri- and tetracyclic compounds in high yields and with excellent stereoselectivities. Cyclic ketones furnish steroid-like compounds with "unnatural" cis/cis annulation of rings B/C/D. The remaining styrene-type double bond of ring B allows further stereoselective reactions. Cases with matched and mismatched relative configuration could be identified leading to dramatic differences in the ring closure ability.
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