Cis selective wittig olefination of .ALPHA.-alkoxy ketones and its application to the stereoselective synthesis of plaunotol.
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概要
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Several Wittig olefinations between α-heterosubstituted acetones and a phosphorus ylide were investigated concerning the product stereoselectivity. Benzyloxyacetone and tetrahydropyranyloxyacetone furnished trisubstituted (<I>Z</I>)-olefins exclusively. The stereoselective preparation of oxygenated acyclic terpenoids was practical by use of the direct Wittig olefination toward α-alkoxy ketones, and it facilitated a total synthesis of plaunotol from geraniol derivatives in short steps with high stereoselectivity.
- 公益社団法人 日本化学会の論文
著者
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Sato Kikumasa
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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Honda Kiyoshi
Department Of Synthetic Chemistry Faculty Of Engineering Yokohama National University
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Inoue Seiichi
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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Iwase Norimichi
Department of Applied Chemistry, Faculty of Engineering, Yokohama National University
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- Cis selective wittig olefination of .ALPHA.-alkoxy ketones and its application to the stereoselective synthesis of plaunotol.