Abstract
Abstract The total synthesis of (±)-arohynapene B, an anticoccidial agent isolated from the fermentation broth of a fungal strain, has been achieved. The tetrahydronaphthalene ring was constructed by the Diels–Alder reaction between dimethyl acetylenedicarboxylate and the 1-(β-acetoxyvinyl)cyclohexene derivative, which was prepared from 3,5-dimethylcyclohexanone via the Ag+-catalyzed rearrangement of the propargylic acetate derivative. The introduction of the dienylcarboxylic acid side chain was accomplished by the Horner–Wadsworth–Emmons olefination repeatedly utilizing ethyl diethylphosphonoacetate. Finally, careful removal of the protecting groups led to (±)-arohynapene B.
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