• Title/Summary/Keyword: Stereoselective synthesis

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Stereoselective synthesis of carbocyclic analogue of Nucleocidin

  • Kim, Ji-Hee;Quan, Ying-Lin;Ko, Ok-Hyun;Hong, Joon-Hee
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.238.3-239
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    • 2003
  • Among 4'-substituted nucleosides. Nucleocidin. 4'-azido thymidine (ADRT), 4'-fluorinated carbocyclic nucleoside. and 3'-fluoro oxetanosin analogue have demonstrated a variety of biological activities. Since the cyclopentane ring of carbocyclic nucleosides can emulate the furanose moiety. a number of these compounds exhibit interesting biological activity, particularly in the areas of antiviral and anticancer chemotherapy. (omitted)

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Synthesis and Antiviral Evaluation of 1'-Branched-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Oh, Chang-Hyun;Yoo, Kyung-Ho;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.31 no.9
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    • pp.2473-2478
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    • 2010
  • Novel 1'-methyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized using an acyclic stereoselective route from commercially available 3,3-diethoxy-propan-1-ol 4. The synthesized nucleoside phosphonate 19 and phosphonic acid 21 were subjected to antiviral screening against various viruses.

Synthesis of 3'(β)-C-methyl Carbodine Analogues as Potential Anti-HCV Agents

  • Li, Hua;Baik, Young-Chan;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.30 no.5
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    • pp.1147-1151
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    • 2009
  • The synthetic route of novel 3′-C-methyl carbodine analogue is described. The construction of tertiary alcohol at 3′- position of carbodine analogues was successfully made via sequential [3,3]-sigmatropic rearrangement, ring-closing metathesis (RCM) and stereoselective dihydroxylation reactions starting from ethyl glycolate.

Synthesis and Antiviral Activity of Novel C-Methyl Branched Cyclopropyl Nucleosides

  • Kwak, Eun-Yee;Hong, Joon-Hee;Park, Young-Jak;Choi, Bo-Gil
    • Archives of Pharmacal Research
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    • v.26 no.9
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    • pp.679-685
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    • 2003
  • A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-Ο-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.

Stereoselective synthesis of novel 4′$\alpha$-C-methyl branched novel carbocyclic nucleosides

  • Kim, Ji-Hee;Ko, Ok-Hyun;Hong, Joon-Hee
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.345.2-345.2
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    • 2002
  • Recently. 4'${\alpha}$-C homologated furanose nucleosides. especially alkyl branches. are molecules of considerable current interest. One of reasons for this prominence arises from the notable biological activities as antiviral and antitumor agents. as shown in 4'${\alpha}$-C-methyl-2-deoxythymidine (EC$_{50}$ = 7.2$\mu$M against HIV in MT-4 cell), 4'${\alpha}$-C-fluoromethyl-2-deoxycytidine. 4'${\alpha}$-C-hydroxymethylthymidine and 4'${\alpha}$- -C-azidomethyl-thymidine. (omitted)omitted)

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Stereoselective Crossed-Aldol Condensation of Hetarylmethyl Ketones with Aromatic Aldehydes in Water : Synthesis of (2E)-3-Aryl-1-hetarylprop-2-en-1-ones

  • Basaif, Salem A.;Sobahi, Tatiq R.;Khalil, Ali Kh.;Hassan, Mohamed A.
    • Bulletin of the Korean Chemical Society
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    • v.26 no.11
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    • pp.1677-1681
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    • 2005
  • Aldol condensation of 2-acetylthiophene, 2-acetylpyrrole and 2-acetylpyridine with different aromatic aldehydes were carried out in water in heterogeneous phases in the presence of cetyltrimethylammonium bromide as cationic surfactant at room temperature. All the reactions occur in a short time with excellent yields of steroselective hetarylpropanones in water as environmental friendly solvent.

Observations Made in Exploring a Pyridinium Salt Photochemical Approach to the Synthesis of (+)-Lactacystin

  • Zhou, Jiwen;Gong, Maozhen;Mariano, Patrick S.;Yoon, Ung-Chan
    • Bulletin of the Korean Chemical Society
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    • v.29 no.1
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    • pp.89-93
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    • 2008
  • The key step in a strategy for the synthesis of (+)-lactacystin involving photocyclization reaction of a cyclopenta-fused pyridinium salt has been probed by using a model substrate. Observations made in this effort led to the discovery of a highly unusual cascade process that leads to stereoselective formation of an interesting tricyclic carbamate. The results of this study are presented and discussed in the context of a (+)-lactacystin synthetic approach.