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Biomedical subjects

CH Cheng

Publications and source records attributed to CH Cheng.

6 recordsLinked to original sources
PubMed2000

Nickel-catalyzed

Oxabenzonorbornadienes 1 and 2 and azabenzonorbornadiene 3 undergo [2+2] cycloaddition with alkynes (PhC triple bond Ph, PhC triple bond CMe, PhC triple bond CCO2Et, PhC triple bond CCH(OEt)2, and HC triple bond C(CH2)4Me) in the presence of [Ni(PPh3)2Cl2], PPh3, and Zn powder in toluene to afford the corresponding exo-cyclobutene derivatives 4a-e, 5a-e, and 6 in fair to excellent yields. Under similar conditions. EtCO2C triple bond CCO2Et does not react with 1 in toluene to give the [2+2] cycloaddition product, but in acetonitrile, the catalytic [2+2] cycloaddition proceeds and cycloadduct 4 f is isolated in 83% yield. At high temperature, these cyclobutene derivatives readily undergo ring expansion to yield the corresponding 8-membered carbocyclic dienes. Thus, flash vacuum pyrolysis of 4a, 4d, 4f, 6, and 14 at 500 degrees C affords dienes 13a-d and 15 in 70-96% yields. This interesting ring expansion may be viewed as the insertion of an alkyne moiety into the carbon-carbon double bond of a cyclic olefin resulting in the enlargement of the ring by two carbons. Compound 13a is readily deoxygenated by TiCl4 and Zn in THF to give a cyclooctatetraene derivative 16 in 89% yield.

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PubMed2000

Ni(II)/Zn-Mediated chemoselective arylation of aromatic aldehydes: facile synthesis of diaryl carbinols

Direct arylation of aromatic aldehydes with aryl bromides in the presence of Ni(II)/Zn was investigated. The choice of ligand in this nickel-catalyzed coupling was critical to the formation of the secondary alcohols. Monodentate phosphine ligands were ineffective, whereas NiBr(2)(dppe)/Zn successfully catalyzed this reductive coupling reaction. The reaction conditions were mild and diarylcarbinols with a variety of functional groups such as ketone, ester, amide, and nitrile groups were readily prepared.

Journal Article↗
PubMed2000

Palladium-Catalyzed Synthesis of 1,3-Dienes from Allenes and Organic Halides.

A wide range of aryl and vinylic halides react with 1,1-dimethylallene (2a) and potassium carbonate in the presence of Pd(dba)(2) (dba = dibenzylideneacetone) in N,N-dimethylacetamide (DMA) at temperature 100-120 degrees C to give the corresponding dienes CH(2)C(CH(3))CRCH(2) (3a-o), where R is aryl or vinylic, in good to excellent yields. Higher yields of diene products were obtained for aryl bromides than for the corresponding aryl iodides and chlorides. Under similar reaction conditions, tetramethylallene (2b), 1-methyl-1-phenylallene (2c), 1-methyl-3-phenylallene (2d), and 1-cyclohexylallene (2e) also react with aryl and vinylic halides to give diene products (3p-w). For 2d, both E and Z isomers 3t and 3u of the diene product were observed. For 2e, two regioisomers 3vand 3w were isolated with 3w likely from alkene isomerization of 3v. Various palladium systems were tested for the catalytic activity of diene formation. In addition to Pd(dba)(2)/PPh(3), Pd(OAc)(2)/PPh(3), PdCl(2)(PPh(3))(2), and PdCl(2)(dppe) are also very effective as catalysts for the reaction of 2a with p-bromoacetophenone (1a) to give 3a. Studies on the effect of solvents and bases show that DMA and K(2)CO(3) are the solvent and base that give the highest yield of diene 3a. Possible mechanisms for this catalytic diene formation are proposed.

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PubMed1999

New guaianolides and xanthine oxidase inhibitory flavonols from ajania fruticulosa

Two new guaianolides (1 and 2) were isolated from the aerial parts of Ajania fruticulosa along with a triterpene (alpha-amyrin), two plant sterols (beta-sitosterol and daucosterol), four flavonols [santin (3), axillarin (4), centaureidin, and 5,7,4'-trihydroxy-3, 3'-dimethoxyflavone], and five sesquiterpenes [ketoplenolide B, 9beta-hydroxyeudesma-4,11(13)-dien-12-oic acid, 9beta-acetoxyeudesma-4,11(13)-dien-12-oic acid, 1alpha,4alpha, 10alpha-trihydroxy-9alpha-angeloyloxyguaia-2,11(13)-dien-12, 6alpha-olide, and 3beta,4alpha-dihydroxyguaia-11(13),10(14)-dien-12, 6alpha-olide]. The structures of the new guaianolides were established as 1alpha-hydroperoxy-4beta,8alpha,10alpha, 13-tetrahydroxyguaia-2-en-12,6alpha-olide (1) and 1alpha-hydroperoxy-4alpha, 10alpha-dihydroxy-9alpha-angeloyloxyguaia-2,11(13)-dien-12, 6alpha-olide (2), respectively. Xanthine oxidase assays of all isolates revealed that santin (3) and axillarin (4) inhibited the enzyme with IC(50) values of 36.5 and 36.0 &mgr;M (that of allopurinol used as a positive control in the study was 24.2 &mgr;M), respectively.

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