62966-23-8Relevant academic research and scientific papers
Acyloxylation of cyclic enones: Synthesis of densely oxygenated guaianolides
Marín-Barrios, Rubén,García-Cabeza, Ana Leticia,Moreno-Dorado, F. Javier,Guerra, Francisco M.,Massanet, Guillermo M.
, p. 6501 - 6509 (2014/08/05)
The α′-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.
Variations of solvent and substitution pattern in Pb(OAc)4 mediated domino reactions
Sesenoglu, Oezge,Candela Lena, Jose I.,Altinel, Ertan,Birlirakis, Nicolas,Arseniyadis, Simeon
, p. 995 - 1015 (2007/10/03)
The effect of solvent on oxidative cleavage of the Hajos-Parrish ketone derived hydrindene-diols 1, and Wieland-Miescher ketone derived octaline-diols 2 with Pb(OAc)4 is presented. Various solvents were screened and compared for these domino reactions. Changing the solvent influenced the reaction rate, product distribution, and chemical yield in the octalin-diol series, while no-effect was detected in the lower homologue hydrindene-diol series. The use of a cheap, readily available chiral carboxylic acid, such as (S)-2-acetoxypropionic acid gave diastereomeric mixtures when performed in the racemic series, offering the potential of a chemical resolution. The influence of the substitution pattern on the substrate was also investigated on variously substituted derivatives of 1. Diols 38 failed to give any detectable amount of IMDA type ring closure, leading only to dialdehyde 39. For the compounds studied, alkyl or carboxyalkyl substituents on the olefin 41 and 44 led to incomplete cascade transformation due to steric interference caused by the alkyl or acyl groups. The oxidative cleavage of unsaturated diols 46 and 48 derived from monocyclic precursors, used as templates to determine whether any unsaturated 1,2-diol could be regarded as a substrate, is also described.
PLE catalysed enantiomeric separation of various (±)-6-acetoxy-α,β-unsaturated cyclic ketones
Tanyeli,Sezen,Dikici,Fleischhauer,Repges,Wang,Gawronski,Kacprzak
, p. 219 - 277 (2007/10/03)
Various (±)-6-acetoxy-α,β-unsaturated cyclic ketones were resolved by PLE catalysed hydrolysis to afford enantiomerically enriched 6-hydroxy derivatives with 85-98% e.e. The absolute configuration of 6-hydroxy-α,β-unsaturated cyclic ketones were determined via CD measurements.
The synthesis of 8,8-disubstituted tricyclic analogs of artemisinin
Haraldson, Chad A.,Karle, Jean M.,Freeman, Sandy G.,Duvadie, Rohit K.,Avery, Mitchell A.
, p. 2357 - 2362 (2007/10/03)
Two tricyclic analogs of artemisinin were designed based on a Comparative Molecular Field Analysis (CoMFA) model, and synthesized for antimalarial testing as part of a program to construct and validate modeling tools for drug design of novel antimlarial agents based on the natural product lead, (+)-artemisinin.
New chiral synthon from the PLE catalyzed enantiomeric separation of 6-acetoxy-3-methylCyclohex-2-en-1-one
Tanyeli, Cihangir,Demir, Ayhan S.,Dikici, Emre
, p. 2399 - 2402 (2007/10/03)
(±)-6-Acetoxy-3-methylcyclohex-2-en-1-one was resolved by PLE catalyzed hydrolysis to afford (+)-6-hydroxy-3-methylcyclohex-2-en-1-one in > 95% e.e. (+)-6-Hydroxy-3-methylcyclohex-2-en-1-one was transformed to its (S)-O-acetyllactyl ester derivative to de
Cleavage of Unsaturated α-Ketols to ω-Oxo-α,β-unsaturated Acids
Floresca, Rey,Kurihara, Masaaki,Watt, David S.,Demir, Ayhan
, p. 2196 - 2200 (2007/10/02)
Sodium periodate is a better reagent than sodium bismutate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated α-ketols and affords ω-oxo-α,β-unsaturated acids in good yield.The combination of this cleavage reaction and a rhodium(I)-m
Hypervalent Iodine Oxidation of α,β-Unsaturated Carbonyl Compounds
Tamura, Yasumitsu,Yakura, Takayuki,Terashi, Hiroaki,Haruta, Jun-Ichi,Kita, Yasuyuki
, p. 570 - 577 (2007/10/02)
Oxidation of non-enolizable α,β-unsaturated carbonyl compounds and enolizable β-monosubstituted α,β-unsaturated carbonyl compounds with phenyl iodine(III) diacetate (PIDA) in methanolic potassium hydroxide gave α-hydroxydimethylacetal β-methoxy products,
OXIDATION OF ENONES TO α'-ACETOXYENONES USING MANGANESE TRIACETATE1
Dunlap, Norma K.,Sabol, Mark R.,Watt, David S.
, p. 5839 - 5842 (2007/10/02)
The oxidation of α,β-unsaturated ketones with manganese (III) triacetate in benzene furnishes α'-acetoxyeneones in good yields.
