Total synthesis of (+/-)-arohynapene B

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-(beta-acetoxyvinyl)cyclohexene d...

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Bibliographic Details
Published inChemistry letters Vol. 34; no. 3; pp. 352 - 353
Main Authors Sugimura, H, Uchida, Y
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 01.03.2005
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary: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-(beta-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.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2005.352