97974-62-4Relevant articles and documents
Oxonium Ion Elektrophiles: Synthesis of the Hypotensive Oudenone.
Bates, Hans, Aaron,Farina, James
, p. 3843 - 3845 (1985)
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-(phenylthio)succinimide to produce 10 followed by oxidation to the corresponding sulfoxide and elimination of phenylsulfenic acid, which produced oudenone(1).