Highly Efficient Synthesis of Conformationally Fixed Bicyclo[3.1.0]hexyl Nucleosides with an Ethenyl Group at C3′-Position as Potential Antiviral Agents 


Vol. 35,  No. 9, pp. 2649-2654, Sep.  2014
10.5012/bkcs.2014.35.9.2649


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  Abstract

Synthesis of north-5′-methylbicyclo[3.1.0]hexyl adenine and hypoxanthine nucleosides with an ethenyl group at C3′ position was successfully achieved by a highly facile method. Methylbicyclo[3.1.0]hexanone (±)-7 with three contiguous chiral centers and its epimer (±)-6 was remarkably simply constructed only by four steps involving a carbenoid insertion reaction in the presence of rhodium (II) acetate dimer as a metal catalyst, giving a correct relative stereochemistry of the generated three chiral centers. Due to steric hindrance from the concave face of the bicyclo[3.1.0]hexanone system, a Grignard reaction of (±)-7 with ethenylmagnesium bromide showed exclusive diastereoselectivity towards the b-face. The Grignard reaction chemoselectively proceeded without reacting with ester functionality. Coupling reaction of glycosyl donor (±)-11 with 6-chloropurine nucleobase afforded only the desired N9-alkylated nucleoside without the formation of N7-regioisomer. By the conventional method, 6-chloro group was converted into 6-amino and 6-hydroxy groups to give the desired adenine and hypoxanthine bicyclo[3.1.0]hexyl carbanucleosides with 3′-ethenyl group, respectively.

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  Cite this article

[IEEE Style]

S. J. Kim, Y. Woo, A. Park, H. R. Kim, S. Son, H. Y. Yun, P. Chun, H. R. Moon, "Highly Efficient Synthesis of Conformationally Fixed Bicyclo[3.1.0]hexyl Nucleosides with an Ethenyl Group at C3′-Position as Potential Antiviral Agents," Bulletin of the Korean Chemical Society, vol. 35, no. 9, pp. 2649-2654, 2014. DOI: 10.5012/bkcs.2014.35.9.2649.

[ACM Style]

Seong Jin Kim, Youngwoo Woo, Ah-Young Park, Hye Rim Kim, Sujin Son, Hwi Young Yun, Pusoon Chun, and Hyung Ryong Moon. 2014. Highly Efficient Synthesis of Conformationally Fixed Bicyclo[3.1.0]hexyl Nucleosides with an Ethenyl Group at C3′-Position as Potential Antiviral Agents. Bulletin of the Korean Chemical Society, 35, 9, (2014), 2649-2654. DOI: 10.5012/bkcs.2014.35.9.2649.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949