• Bulletin of the Korean Chemical Society
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• 제28권10호
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• pp.1645-1650
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• 2007

This paper describes a racemic and stereoselective synthetic route for a novel cyclohexenyl carbocyclic adenine analogue. The required stereochemistry of the target compound was controlled using a stereoselective glycolate Claisen rearrangement followed by α-chelated carbonyl addition. The introduction of 6-chloropurine was achieved using Mitsunobu conditions, and further modifications of the corresponding heterocycle gave the target cyclohexenyl nucleoside.

• Bulletin of the Korean Chemical Society
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• 제26권11호
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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.

• Bulletin of the Korean Chemical Society
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• 제27권7호
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• pp.976-980
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• 2006

The synthesis of 4'-phenyl and 1'-methyl doubly branched carbocyclic nucleoside was accomplished from 2-hydroxy acetophenone. The 4'-phenyl group was installed via a [3,3]-sigmatropic rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. Cyclization of divinyl 9 was performed using $2^{nd}$ generation Grubbs catalyst. The coupling of cyclopentenol 12$\alpha$ with 6-chloropurine by Mitsunobu reaction and desilylation was used to synthesize the target nucleoside 15.