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

Full Text: HTML

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 ...

Related Articles:

Rhodium-Catalyzed Hydroformylation of Allyl Alcohol. A Potential Route to1, 4-Butanediol

[Pittman, Charles U.; Honnick, William D. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2132 - 2139]

Rhodium-Catalyzed Hydroformylation of Allyl Alcohol. A Potential Route to1, 4-Butanediol

[Pittman, Charles U.; Honnick, William D. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2132 - 2139]

A study of the catalytic deuteration of 1, 4-butynediol

[Chickos, James S.; Uang, Jack Y.-J.; Keiderling, Tim A. Journal of Organic Chemistry, 1991 , vol. 56, # 7 p. 2594 - 2596]

Rhodium-Catalyzed Hydroformylation of Allyl Alcohol. A Potential Route to1, 4-Butanediol

[Pittman, Charles U.; Honnick, William D. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2132 - 2139]

Synthesis and kinetic studies of a simple prostacyclin model

[Bergman, Nils-Ake; Jansson, Marie; Chiang, Yvonne; Kresge, A. Jerry; Yin, Ya Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4449 - 4453]

More Articles...