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Synthesis Of Medium‐Sized 2,ω‐cis‐Disubstituted Cyclic Ethers By Reductive Cyclization Of Hydroxy Ketones

Gloria Hernández-Torres, J. Mateo, F. Colobert, A. Urbano, M. Carreño
Published 2016 · Chemistry

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The synthesis of 7-, 8- and 9-membered cyclic ethers isolaurepan, lauthisan and obtusan was achieved through the cis-stereoselective TMSOTf/Et3SiH promoted reductive cyclization of the corresponding saturated hydroxy ketones, available in three steps from commercial starting materials: oxirane opening with lithium acetylide, Rh-catalyzed conjugate addition of the terminal alkynes to the corresponding unsaturated ketones and triple bond hydrogenation.
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