• Bulletin of the Korean Chemical Society
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• 제26권12호
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• pp.1933-1936
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• 2005

Total synthesis of biologically interesting $({\pm})$-cannabichromene, $({\pm})$-cannabichromenic acid, and $({\pm})$-daurichromenic acid is described. The key step in the synthetic strategy involves the formation of benzopyrans by ethylenediamine diacetate-catalyzed reactions of resorcinols with $\alpha$,$\beta$-unsaturated aldehydes.

• Bulletin of the Korean Chemical Society
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• 제32권2호
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• pp.566-570
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• 2011

An efficient and general synthesis of bibenzyl derivatives bearing pyranyl rings was achieved by ethylenediamine diacetate-catalyzed reactions of 3,5-dihydroxybibenzyl with ${\alpha},{\beta}$-unsaturated aldehydes in moderate yields. These reactions provided naturally occurring compounds 1 and 2 in single step reaction. As an application of this methodology, biologically interesting natural bauhinol D (8) was synthesized by a convergent sequence from readily available benzaldehyde and benzyl phosphonate.

• Bulletin of the Korean Chemical Society
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• 제23권7호
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• pp.998-1002
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• 2002

An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of $\alpha\beta-unsaturated$, aldehydes in moderate yields. This method has been applied to the synthesis of pyranocoumar ins, pyranophenalenones, and pyranoquinolinone alkaloids.

• 한국축산식품학회지
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• 제23권1호
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• pp.86-95
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• 2003

비타민 E에 의한 육색소의 산화 안정성 향상 기작을 정리하였다. 지용성 산화제인 $\alpha$-토코페롤이 수용성 단백질인 옥시마이오글로빈을 보호하는 원리가 밝혀지고 있다. 최근의 연구들에서 $\alpha$-토코페롤이 세포막 지방산화의 2차 산화물들의 방출을 지연시켜 옥시마이오글로빈 산화를 억제시키고 식육의 바람직한 육색을 유지시킨다는 증거가 제시되고 있다. 지방산화물의 한 그룹인 $\alpha$,$\beta$-분포화 알데하이드들은 단백질과 서로 결합하는 역할을 하여 옥시마이오글로빈의 산화를 증진시키는 것으로 밝혀졌다. 만약 $\alpha$-토코페롤이 이런 활동적인 알데하이드들의 발생을 지연시킨다면 이런 지방산화물들이 옥시마이오글로빈의 산화에 미치는 영향도 억제될 것이다. 또한$\alpha$-토코페롤은 메트마이오글로빈의 환원에 작용하여 쇠고기의 육색 안정성 유지에 일정부분 역할을 담당하는 것으로 사료된다.

• Journal of Ginseng Research
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• 제38권1호
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• pp.34-39
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• 2014

Cigarette smoke is considered a major risk factor for vascular diseases. There are many toxic compounds in cigarette smoke, including acrolein and other ${\alpha},{\beta}$-unsaturated aldehydes, which are regarded as mediators of inflammation and vascular dysfunction. Furthermore, recent studies have revealed that acrolein, an ${\alpha},{\beta}$-unsaturated aldehyde in cigarette smoke, induces inflammatory mediator expression, which is known to be related to vascular diseases. In this study, we investigated whether Korean Red Ginseng (KRG) water extract suppressed acrolein-induced cyclooxygenase (COX)-2 expression in human umbilical vein endothelial cells (HUVECs). Acrolein-induced COX-2 expression was accompanied by increased levels of phosphorylated p38 in HUVECs and KRG inhibited COX-2 expression in HUVECs. These results suggest that KRG suppresses acrolein-induced COX-2 expression via inhibition of the p38 mitogen-activated protein kinase signaling pathway. In addition, KRG exhibited an inhibitory effect on acrolein-induced apoptosis, as demonstrated by annexin Vepropidium iodide staining and terminal deoxynucleotidyl transferase-mediated dUTP nick end-labeling assay. Consistent with these results, KRG may exert a vasculoprotective effect through inhibition of COX-2 expression in acrolein-stimulated human endothelial cells.

• Bulletin of the Korean Chemical Society
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• 제32권1호
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• pp.219-224
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• 2011

The new MPV type reagent, Al-trifluoromethanesulfonyldiisobutylalane ($DIBAO_3SCF_3$), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined, and compared its reactivity with that of Al-methanesulfonyldiisobutylalane ($DIBAO_3SCH_3$) in order to understand the fluorine-substituent effect on its reactivity. In general, the reactivity of $DIBAO_3SCF_3$ appears to be much higher than that of $DIBAO_3SCH_3$, apparently due to the acidity increase by the electron-withdrawing fluorine-substituent. The reagent reduced aldehydes and ketones readily, but showed a perfect selectivity in the reduction of $\alpha,\beta$-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in an absolutely 100% purity. In addition, the reagent achieved the regioselective cleavage of phenyl- or/and alkyl-substituted epoxides to the less substituted alcohols in a perfect regioselectivity. Moreover, the reagent also showed an high stereoselectivity in the reduction of substituted cycloalkanones to produce the thermodynamically more stable alcohol epimers exclusively.

• Bulletin of the Korean Chemical Society
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• 제31권4호
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• pp.840-844
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• 2010

The new MPV type reagent, Al-methanesulfonyldiisobutylalane ($DIBAO_3SCH_3$), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of $\alpha,\beta$-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, $DIBAO_3SCH_3$ shows a high stereoselectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.

• Bulletin of the Korean Chemical Society
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• 제8권4호
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• pp.313-318
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• 1987

The approximate rate and stoichiometry of the reaction of excess Thexylbromoborane-methyl sulfide, $ThxBHBr{\cdot}SMe_2,$ with selected organic compounds containing representative functional groups under standardized conditions (methylene chloride, $0^{\circ}C)$ were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The selectivity of the reagent was also compared to the selectivity of thexylchloroborane-methyl sulfide. Thexylbromoborane appears to be a much milder and hence more selective reducing agent than thexylchloroborane. The reagent tolerates many organic functionalities. Thus, the reagent shows very little reactivity or no reactivity toward acid chlorides, esters, epoxides, amides, nitro compounds including simple olefins. However, this reagent can reduce aldehydes, ketones, carboxylic acids, nitriles, and sulfoxides. Especially the reagent reduces carboxylic acids including ${\alpha},{\beta}$ -unsaturated ones and nitriles to the corresponding aldehydes. In addition to that, thexylbromoborane shows good stereoselectivity toward cyclic ketones, much better than the chloro-derivative.

• 통합자연과학논문집
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• 제1권3호
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• pp.192-194
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• 2008

A series of non-free hydride reducing systems containing boron or aluminum atom, which possess no metal-hydride bond but an available hydrogen at a branched ${\beta}$-position, has been applied to the selective reduction (chemo--, regio-, and stereoselective reduction) of organic compounds. The systems, comprised of diisopinocampheylborane and diisobutylalane derivatives, exhibited almost perfect selectivities in the reduction of aldehydes and ketones. The characteristics features of this systems leading to a perfect transformation have been depicted in this report, especially in the 1) Reduction of ${\alpha}$,${\beta}$-Unsaturated Carbonyl Compounds to Allylic Alcohols via 1,2-Reduction, 2) Chemoselective Reduction between Structurally Different Carbonyl Compounds, and 3) Stereoselective Reduction of Cyclic Ketones.

• Bulletin of the Korean Chemical Society
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• 제31권10호
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• pp.2961-2966
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• 2010

Reduction of carbonyl compounds such as aldehydes, ketones, $\alpha,\beta$-unsaturated enals and enones, $\alpha$-diketones and acyloins was carried out readily with $NaBH_3CN$ in the presence of wet $SiO_2$ as a neutral media. The reactions were performed at solvent-free conditions in oil bath (70 - $80^{\circ}C$) or under microwave irradiation (240 W) to give the product alcohols in high to excellent yields. Regioselective 1,2-reduction of conjugated carbonyl compounds took place in a perfect selectivity without any side product formation.