• Bulletin of the Korean Chemical Society
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• 제6권2호
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• pp.86-90
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• 1985

(Z)-13-Eicosen-10-one, an active component of the sex pheromone of the peach fruit moth was synthesized from 4-oxo-tridecan-1-al and heptylidenetriphenylphosphonium ylide by Wittig reaction. The key intermediate, 4-oxo-tridecan-1-al, was synthesized by three different methods. The biological activity test of the synthetic pheromone as attractant for the male peach fruit moth was tested at several districts in Korea.

• Bulletin of the Korean Chemical Society
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• 제14권1호
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• pp.32-38
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• 1993

3-(3-Bromotetrahydrofuran-2-yl)-3-cephem 7 was obtained from 3-(2-hydroxyethyl)vinyl-3-cephem 6 by the cyclization reaction using N-bromosuccinimide. Compound 5 was prepared by Wittig reaction, namely a coupling of cephem-derived triphenylphosphonium salt 3 with aldehyde component 4 in the presence of base.

• Bulletin of the Korean Chemical Society
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• 제20권8호
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• pp.929-934
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• 1999

2-( β-Alkoxyvinyl)-4-(1-hydroxyalkyl)pyrroles (14) were synthesized from 4-acylpyrrole-2-carboxylates (8) by sequential reduction of their acyl and alkoxycarbonyl groups to give 4-(1-hydroxyalkyl)pyrrole-2-carbalde-hydes (13) followed by Wittig reaction of the aldehydes with the ylide of alkoxymethylphosphonium chloride. Diels-Alder reaction of 2-(β-alkoxyvinyl)-4-(1-hydroxyalkyl)pyrroles with trans-methyl β-nitroacrylate gave 6-alkoxy-3-(1-hydroxyalkyl)-5-nitro-4,5,6,7-tetrahydroindole-4-carboxylates (3).

• Bulletin of the Korean Chemical Society
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• 제17권2호
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• pp.153-158
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• 1996

The synthesis of common skeleton of podosporin A and aureol was studied through cationic olefin cyclization as a key step. The generation of thermodynamic silyl enol ether or enol acetate under known conditions gave regioselectivity of 88:12. The enolate alkylation of 2,3-dimethylcyclohexanone with 2,5-dimethoxybenzyl bromide at the more substituted site via lithium enolate gave poor yield. In this case an organozincate or an ammonium enolate also proved to be ineffective or not practical in terms of yield. Side chain elongation of the substituted cyclohexanone 13 through Grignard reaction, Wittig reaction, or Shappiro reaction did not proceed because of steric hindrance and side reactions. However, Stille coupling reaction via enol triflate produced the desired product 18 in high yield. The advanced intermediate 22, which was efficiently synthesized from 18, produced 24 instead of the desired product under a cationic olefin cyclization condition, indicating that the cyclization occurred in a stepwise mannervia the organomercury intermediate 23.

• 약학회지
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• 제30권6호
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• pp.329-333
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• 1986

6-[3-(Hydroxymethyl)-2, 3-epoxybutyl]-3, 5-dimethoxyphenol was synthesized by means of the eight steps, such as allylether, Claissen rearrangement, tosylation, oxidation, Wittig reaction, reduction and epoxidation from 3, 5-dimethoxyphenol. The epoxidation of 6-[3- (hydroxymethyl)-2-butenyl]-3,5-dimethoxy phenol using the L-(+)-diethyltartrate(DET), titanium (IV) isopropoxide Ti[(O-iPr)$_4$] and t-butylhydroperoxide(TBHP) is described.

• Bulletin of the Korean Chemical Society
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• 제22권5호
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• pp.476-480
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• 2001

4-Thiazolidinones which are hetarylsubstituted at the 2-position were prepared by the reaction of mercapto acids with aldimines which were prepared by the condensation of pyrrole-2-carbaldehyde with different aromatic amines. After their benzylide ne derivatives were obtained, we first applied the Wittig reagent on them in the presence of triethylamine, dihydrofurothiazolidines were synthesized. Second, we prepared new pyrazolinothiazolidines by using phenylhydrazine in the presence of sodium acetate. All mentioned compounds have been characterized by their spectral data, and screened for their antimicrobial activities. Some of them exhibit moderate to good antibacterial and tuberculostatic activities.

• Bulletin of the Korean Chemical Society
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• 제10권4호
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• pp.366-368
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• 1989

The 3-formyl-2-cephem 4, available from 7-aminocephalosporanic acid has been converted to C-3 vinylic cephems. The reactions involved are the Grignard addition to 4, the conversion of the resulting alcohols to mesylates, and the elimination of the mesyl group by LiCl. When ethylmagnesium iodide is used, only 3-[(E)-1-propenyl] cephem is obtained, which is not easily available by conventional Wittig reaction.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.362.2-362.2
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• 2002

Antofine belongs to the Phenathroindolizidine group of alkaloids. This natural products exhibit interesting biological properties such as antitumour activity. and anti-inflammentory. Wittig reaction of phenathrenealdehyde with the phosponium salt provided the phenathreneazidealkene in good yield. Intramolecular 1.3-dipolar cycloaddition of the resulting azidealkent in refluxing benzene proceeded the imine. It was reduced with cyanoborohydride of Noyori's Asymmetric Hydrogenation. (omitted)

• 공업화학
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• 제29권3호
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• pp.303-306
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• 2018

DMT 생산과정의 부산물로서 폐기 처리되어 왔던 methyl 4-formylbenzoate (MFB)를 출발 물질로 하여 고급 형광 증백제 family와 동일한 4,4'-di((E)-styryl)-1,1'-biphenyl 기본 골격을 갖고 aromatic ester가 도입된 새로운 형광 증백제(fluorescent whitening agent) 후보 물질 6종을 합성하였다. 후보 물질 6종은 MFB 및 그의 유도체와 tetraethyl biphenyl-4,4'-diylbis(methylene)diphosphonate와 Wittig-Horner 반응을 이용하여 합성하였다. 합성된 6종에 대하여 형광증백제로의 가능성을 확인하기 위하여 UV 스펙트럼을 기록하여 흡광 계수를 얻었으며, 6종 모두 전반적으로 기존 상용 제품(log ${\varepsilon}$ 4.85)과 유사한 몰 흡광 계수(log ${\varepsilon}$ 4.59~5.00)를 보여주고 있다. 특별히 화합물 디메톡시 페닐그룹을 갖는 16, 17은 기존 상용 제품보다 우수한 몰흡광 계수를 나타내고 있어 상용화를 위한 현장 테스트를 진행할 예정이다.

• 공업화학
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• 제28권3호
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• pp.294-298
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• 2017

Dimethyl terephthalate (DMT) 생산과정의 부산물로서 폐기 처리되어왔던 methyl 4-formylbenzoate (MFB)를 출발 물질로하여 고급 형광증백제 family인 Uvitex FP와 동일한 4,4'-di((E)-styryl)-1,1'-biphenyl 기본 골격을 갖는 새로운 형광증백제(fluorescent whitening agent) 후보 물질 6종을 합성하였다. 후보 물질 6종은 MFB 및 그의 유도체와 tetraethyl biphenyl-4,4'-diylbis(methylene) diphosphonate (3)와 Wittig-Horner 반응을 이용하여 합성하였다. 합성된 6종에 대하여 형광증백제로의 가능성을 확인하기 위하여 UV spectrum을 기록하여 몰흡광 계수를 얻었으며, 6종 모두 Uvitex FP 127(log ${\varepsilon}$ 4.85)보다 낮은 몰흡광 계수(log ${\varepsilon}$ 3.95~2.60)를 보임으로서 형광증백제로는 적합하지 못한 것을 확인하였다.