H. Sugimura, Y. Uchida
Feb 5, 2005
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0
Influential Citations
4
Citations
Journal
Chemistry Letters
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 (′)-aro-hynapene B.