Synthesis and applications of angular acyl-substituted azulenones: formal synthesis of (±)-acorenol and facile access to the hydroazulene core of pseudolaric acid

Azulenones with an angular acyl substituent were synthesized by the reactions of 2-aryl-2-chloroacylketenes with phenylthioacetylene or ethoxyethyne. Acyl-substituted azulenones with a methoxy group in the cycloheptatriene moiety could be rearranged to spiro4.5] compounds. Spiro4.5] and bicyclo5.3.0]decane ring systems were constructed en route to a formal synthesis of (±)-acorenol and synthesis of the hydroazulene core of pseudolaric acid, respectively.