Synthesis of Z,Z-Trishomofarnesal tert-butylimine
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A highly stereoselective method was developed for the preparation of Z,Z-trishomofarnesal tert-butylimine, a key block synthone required for the construction of polyprenols with a nonnatural configuration of the “head” end of the chain, using as a basis the controlled condensation of aldehydes with aldimines. It was shown that introduction into the condensation of aldehydes containing an acetal grouping at the ω-position results in the formation of considerable amounts of aldols. The use of α-trimethylsilyl derivatives of aldimines makes it possible to dispense with this process and to direct the reaction toward the desired Eacroleins.
KeywordsAcetal Aldehyde Aldol Acetal Grouping Aldimines
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