• Proceedings of the PSK Conference
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• 2001.04a
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• pp.105.1-105.1
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• 2001

• Bulletin of the Korean Chemical Society
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• v.34 no.9
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• pp.2815-2818
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• 2013

• YAKHAK HOEJI
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• v.47 no.5
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• pp.271-275
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• 2003

Easy and efficient synthetic route of novel 4'-C methyl branched carbocyclic nucleosides is described. The installation of alkyl and aryl groups at 4'-position of carbocyclic nucleosides were successfully made via sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) starting from simple ketones such as acetol. Adenine and uracil were coupled via Pd(0) catalyzed reaction, followed by desilylation to give novel compounds 13 and 14, respectively.

• Bulletin of the Korean Chemical Society
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• v.25 no.11
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• pp.1720-1722
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• 2004

• Bulletin of the Korean Chemical Society
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• v.25 no.11
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• pp.1726-1728
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• 2004

• Archives of Pharmacal Research
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• v.18 no.3
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• pp.217-218
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• 1995

• Journal of the Korean Chemical Society
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• v.30 no.6
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• pp.548-552
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• 1986

A stereoselective synthesis of 3-phenoxybenzyl (${\pm}$)-cis and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid starting from readily available 2-methyl-3-buten-2-ol($\underline{2}$) is described. Allylic rearrangement of 2-methyl-3-buten-2-ol, in the presence of acetic acid and acetic anhydride gave 3-methyl-2-butenyl acetate($\underline{3}$). The [3,3] sigmatropic rearrangement of the allyl acetate($\underline{3}$), as the silylketene acetal, produced the ${\gamma},\;{\delta}$-unsaturated acid($\underline{4}$). Treatment of 3,3-dimethyl-4-pentenoic acid($\underline{4}$) with SOCl2 followed by esterification with 3-phenoxybenzyl alcohol yielded 3, 3-dimethyl-4-pentenoic acid ester($\underline{5}$). Addition of carbon tetrachloride to the olefin ester($\underline{6}$) furnished 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid ester ($\underline{7}$). Cyclization with potassium t-butoxide and elimination of hydrogen chloride afforded 3-phenoxybenzyl (${\pm}$) cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid.

• Bulletin of the Korean Chemical Society
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• v.26 no.11
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• pp.1767-1770
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• 2005

Novel 1',4'-dimethyl branched carbocyclic nucleosides were synthesized from acetol. The 4'-methyl group was installed via a Claisen rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. The coupling of nucleosidic bases and desilylation was used to produce a series of novel nucleosides.

• Archives of Pharmacal Research
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• v.13 no.2
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• pp.201-203
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• 1990

The efficient synthetic routes to cis-1-ethenyl-2-hydroxymethyl-cyclohexane, an useful synthetic intermediate, have been described. Access to the cis-disubstituted cyclo hexane is gained through the Clasen rearrangment and selective DHP protection of diol respectively.

• Bulletin of the Korean Chemical Society
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• v.25 no.2
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• pp.221-225
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• 2004

A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- ${\gamma}$-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine ($N^4$-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.