The Journal of Organic Chemistry

Oxonium ion electrophiles: synthesis of the hypotensive oudenone

HA Bates, J Farina

Index: Bates, Hans, Aaron; Farina, James Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3843 - 3845

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Citation Number: 20

Abstract

The hypotensive oudenone (1) has been synthesized through the intermediacy of oxonium ion 4. Acid-catalyzed C-alkylation of 1, 3-cyclopentanedione (3) with 5-propyltetrahydro-2- furanol (6b) afforded dihydrooudenone 2b. In contrast, alkylation of 3 with 2-chloro-5- propyltetrahydrofuran (7b) was unsuccessful. Unsaturation was introduced into 2b by treatment with N-(pheny1thio) succinimide to produce 10 followed by oxidation to the ...