• Title/Summary/Keyword: Efficient cyclization

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Mn(III)-Mediated Radical Cyclization for Δ1-3-Octalone Synthesis

  • Lee, Mi-Ai;Yang, Jae-Deuk;Kim, Moon-Soo;Jeon, Hye-Sun;Baik, Woon-Phil;Koo, Sang-Ho
    • Bulletin of the Korean Chemical Society
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    • v.23 no.5
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    • pp.736-740
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    • 2002
  • An efficient and practical synthetic method of △1 -3-octalone, which is a versatile building block for thesyntheses of polycyclic compounds, has been developed. The dianion of ethyl acetoacetate reacts with cyclohexene-1-carboxaldehyde (3) to produce the aldol adduct 6, which then undergoes Mn(Ⅲ)-mediated radical cyclization followed by acetate elimination to give △1 -3-octalone 4. A detailed mechanistic insight of Mn(Ⅲ)-mediated cyclization of 6 has been disclosed.

Total Synthesis of Fentanyl

  • Suh, Young-Ger;Cho, Kyung-Ho;Shin, Dong-Yoon
    • Archives of Pharmacal Research
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    • v.21 no.1
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    • pp.70-72
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    • 1998
  • Fentanyl of a potent anilidopiperidine analgesic has been synthesized from a simple phenyle-thylamine by four step sequence. The key part of this synthesis involves an efficient construc-tion of phenylethylpiperidone skeleton via aminomethano desilyation-cyclization followed by Swern oxidation.

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Synthesis of Carbocycles Using Metal Catalyst(I) -Stereoselective Synthesis of Cyclopentane Using Pd(0) Catalyst- (금속 촉매를 이용한 Carbocycle의 합성(I) -Pd(0) 촉매를 이용한 Cyclopentane의 입체선택적 합성-)

  • Suh, Young-Ger;Lee, Gi-Ho;Cho, Youn-Sang
    • YAKHAK HOEJI
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    • v.34 no.5
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    • pp.287-290
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    • 1990
  • An efficient stereoselective synthetic route to carbocycle is described. 1,1,2-Trisubstituted cyclopentane was synthesized from allylic carbonate by Pd(0) catalyzed cyclization.

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Approach to the Total Synthesis of Acanthoside-D

  • Ngoc, Thyen-Truong;Park, Hae-Il
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.186.4-187
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    • 2003
  • Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

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Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides

  • Mo, Jun-Tae;Hwang, Hoon;Lee, Phil-Ho
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.2911-2915
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    • 2011
  • Efficient synthetic method for the preparation of ethyl 2-aryl-2,3-alkadienoates through Pd-catalyzed selective allenyl cross-coupling reactions of aryl iodides with organoindiums generated in situ from indium and ethyl 4-bromo-2-alkynoate was developed. The cyclization reaction of ethyl 2-aryl-2,3-alkadienoates catalyzed by $AuCl_3$ and AgOTf in the presence of AcOH or TfOH produced various ${\alpha}$-aryl ${\gamma}$-butenolides or ${\gamma}$-substituted ${\alpha}$-aryl ${\gamma}$-butenolides.

An Efficient Synthesis of Substituted Furans by Cupric Halide-Mediated Intramolecular Halocyclization of 2-(1-Alkynyl)-2-alken-1-ones

  • Fu, Wei-Jun;Xu, Feng-Juan;Guo, Wen-Bo;Zhu, Mei;Xu, Chen
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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    • pp.887-891
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    • 2013
  • An efficient synthesis of 3-halofurans by the intramolecular cyclization of 2-(1-alkynyl)-2-alken-1-ones with cupric halide has been developed. A broad range of 3-chloro- and 3-bromofuran derivatives could be obtained in the present method in moderate to good yields. The 3-halofuran derivatives are potential synthetic intermediates for amplification of molecular complexity.

A Facile and Efficient Synthesis of Dronedarone Hydrochloride

  • Li, Feng;Jin, Chunhua;Zou, Jianwei;Wu, Jun
    • Bulletin of the Korean Chemical Society
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    • v.35 no.7
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    • pp.1970-1972
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    • 2014
  • A facile and efficient synthesis of dronedarone hydrochloride starting from commercially available 4-nitrophenol is described. This approach features a tandem-type synthesis of 3-carbonylated benzofuran involving cyclization of 2-ethynylphenol followed by $CO_2$ fixation at the 3-position of the benzofuran ring mediated by potassium carbonate without the addition of any transition metal catalyst.

Efficient Cyclization of Substituted Diphenols : Application to the Synthesis of Sulforhodamine B (치환 다이페놀의 효율적 고리화 반응: 설퍼로다민B의 합성에의 응용)

  • Park, Min Kyun;Shim, Jae Jin;Ra, Choon Sup
    • Clean Technology
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    • v.21 no.2
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    • pp.102-107
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    • 2015
  • Rhodamine dyes are widely used as fluorescent probes because of their excellent photophysical properties, such as high extinction coefficients, excellent quantum yields, great photostability, relatively long emission wavelengths. A great synthetic effort has been focused on developing efficient and practical procedures to prepare rhodamine derivatives, because for most applications the probe must be covalently linked to another (bio)molecule or surface. Sulforhodamine B is one of the most used rhodamine dyes for this purpose, because it carries two sulfoxy functions which can be easily utilized for binding with other molecules. Recently, we needed an expedient, practical synthesis of sulforhodamine derivatives. We found the existing procedure for obtaining those compounds unsatisfactory, particularly, with the cyclization process of the dihydroxytriarylmethane (1) to produce the corresponding xanthene derivative (2). We report here our findings, which represent modification of the existing literature procedure and provide access to the corresponding xanthene derivative (2) in a high yield. Use of methanol as a co-solvent was found quite effective to prohibit the water molecule produced during the cyclization reaction from retro-cyclizing back to the starting dihydroxytriarylmethane and the yield of the cyclization was increased (up to 84% from less than 20%). The reaction temperature was significantly lowered (80 vs. 135 ℃). Thus, the reaction proceeds in a higher yield and energy-saving manner where the use of reactants and the production of chemical wastes is minimized.