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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 9
BKCSDE 35(9)
September 20, 2014 

Highly Efficient Synthesis of Conformationally Fixed Bicyclo[3.1.0]hexyl Nucleosides with an Ethenyl Group at C3′-Position as Potential Antiviral Agents
Seong Jin Kim, Youngwoo Woo, Ah-Young Park, Hye Rim Kim, Sujin Son, Hwi Young Yun, Pusoon Chun, Hyung Ryong Moon*
5-Methylbicyclo[3.1.0]hexanone, Carbenoid cycloaddition, 3′-Ethenyl, North conformation, Mitsunobu reaction
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.
2649 - 2654
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