Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ

Lijun Liu Lanzhou University, State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou, 730000, P.R. China

Fajun Nan Lanzhou University, State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou, 730000, P.R. China

Zhaoming Xiong Lanzhou University, State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou, 730000, P.R. China

Tongshuang Li Department of Chemistry, Hebei University, Baoding, 071002, P. R. China

Yulin Li Lanzhou University, State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou, 730000, P.R. China

Abstract

9-Acetoxy-eudesma-4, 11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesma-4, 11-dien-3-ones (5a, 5b) were treated with DDQ in dioxane to yield normal 1,2-dehydro-products, whereas 14-noreudesma-4, 11-dien-3, 9-diones (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreudesma-1, 3, 5 (10), 11-tetraen-9-one(3). No reaction was observed by treatment of eudesma-4, 11-dien-3, 9-diones (1a, 1b) with DDQ under the same conditions. The effect of 10-methyl configuration on this reaction is also discussed.

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Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ

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Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ

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