Acetoxyl group directed cyclization promoted by SmI2: directing group determined stereocomplementarity |
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| Authors: | Kan Toshiyuki Hosokawa Seijiro Nara Shinji Tamiya Hiroaki Shirahama Haruhisa Matsuda Fuyuhiko |
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| Institution: | Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. |
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| Abstract: | Complete reversal of diastereoselectivity was observed in the SmI(2)-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI(2)-induced ketyl-olefin coupling cyclizations of the delta-hydroxy ketone 1 and delta-acetoxy ketone 3. |
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