Short Syntheses of (±)‐Grandisol and (±) Lineatin via , a common Intermediate

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.