Short Syntheses of (±)-Grandisol and (±) Lineatin via,a common Intermediate |
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Authors: | Ivana Aljancic-Solaja Max Rey Andr S Dreiding |
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Institution: | Ivana Aljancic-Solaja,Max Rey,André S. Dreiding |
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Abstract: | A 6-step synthesis of (±)-grandisol ( 1 ) is presented, which involves dichloroketene addition to 3-methyl-3-butenyl acetate ( 4 ), reductive dechlorination of the adduct 6 to the ketone 7 and saponification to 8 , aldolization of 7 or 8 with acetone and cyclization to the bicyclic ketone 9 , Wolff-kishner, reduction to 14 , and finally ring opening to 1. Since 9 is a known intermediate of the synthesis of (±)-lineatin ( 2 ), the latter can now be obtained in 6 steps. |
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