34348-59-9Relevant articles and documents
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives
Pennell, Matthew N.,Turner, Peter G.,Sheppard, Tom D.
experimental part, p. 4748 - 4758 (2012/05/04)
A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer-Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.
Biological evaluation of isoegomaketone isolated from perilla frutescens and its synthetic derivatives as anti-inflammatory agents
Park, Yong Dae,Jin, Chang Hyun,Choi, Dae Seong,Byun, Myung-Woo,Jeong, Il Yun
experimental part, p. 1277 - 1282 (2012/05/20)
The anti-inflammatory activities of a prepared isoegomaketone 3a and its derivatives 3b-3f were evaluated in RAW 264.7 cells. Among these, the compound 3d was displayed the most potent inhibitory activities against production of nitric oxide, monocyte chemoattractant protein- 1 and interleukin-6. Based on these results, the abilities of compounds 3a-3f to modulate NF-κB and AP-1-mediated gene transcription using a luciferase reporter assay were investigated. The transcriptional activities of NF-κB and AP-1 decreased when pretreated with 3a- 3f. Interestingly, at 10 μM, compound 3d markedly suppressed the lipopolysaccharide-induced NF-κB and activator protein-1 DNA binding activities. Some preliminary structure-activity relationships were proposed that may provide a direction for further study.
PALLADIUM MEDIATED SYNTHESIS OF CONJUGATED E or Z ENONES AND UNSYMMETRICAL DIVINYL KETONES. ONE-POT PREPARATION OF ISOEGOMAKETONE
Jabri, N.,Alexakis, A.,Normant, J. F.
, p. 1369 - 1380 (2007/10/02)
The palladium (o) catalyzed coupling of acyl halides or anhydrides with alkenyl copper reagents furnishes α,β ethylenic ketones and α,β-α',β' diethylenic ketones in high yield.The substitution pattern of the alkenyl copper reagent, directly obtained by carbocupration of alkynes, is fully retained.Anhydrides of Z-ethylenic acids also retain their Z stereochemistry. β-halogeno-vinyl ketones react under the above conditions to afford α,β-γ,δ dienones.An efficient one-pot synthesis of Z or E isoegomaketone is reported.
