Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker |
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Authors: | Chang Yi-Fan Liu Chen-Yu Guo Chih-Wei Wang Yen-Chih Fang Jim-Min Cheng Wei-Chieh |
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Institution: | The Genomics Research Center, Academia Sinica, Nankang, Taipei, 115, Taiwan. |
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Abstract: | Solid-phase organic synthesis of polyprenols with a traceless sulfone linker is described. The polymer-bound benezenesulfinate is first linked with the "tail" building blocks of isoprenyl chlorides via S-alkylation. With use of dimsyl anion as an appropriate base, the polymer-bound alpha-sulfonyl carbanion is generated and coupled with other "body" building blocks in an efficient manner. After repeated processes and a global palladium-catalyzed desulfonation with LiEt 3BH as the reducing agent, the desired polyprenols with various chain lengths and geometrical configurations are obtained in 32-59% overall yields. The solid-phase synthesis offers the advantage in facile isolation of polyprenols without tedious operation or time-consuming purification. |
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