STUDIES ON THE DEHYDROGENATION OF 9-OXYGENATED-EUDESMA-4-EN-3-ONES WITH DDQ

Authors
LIU LJ NAN FJ XIONG ZM LI TS LI YL
Citation
Lj. Liu et al., STUDIES ON THE DEHYDROGENATION OF 9-OXYGENATED-EUDESMA-4-EN-3-ONES WITH DDQ, Synthetic communications, 26(3), 1996, pp. 551-557
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
26
Issue
3
Year of publication
1996
Pages
551 - 557
Database
ISI
SICI code
0039-7911(1996)26:3<551:SOTDO9>2.0.ZU;2-O
Abstract
9-Acetoxy-eudesma-4,11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesm a-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-dione s (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreud esma-1, 3, 5 (10), 11-tetraen-9-one (3). No reaction was observed by t reatment of eudesma-4,11-dien-3,9-diones (1a, 1b) with DDQ under the s ame conditions. The effect of 10-methyl configuration on this reaction is also discussed.