Synthesis of carbocyclic nucleoside precursors from bicyclo[2.2.1]hept-5-enes using a novel reductive C-C bond cleavage reaction.
Dimethyl c-4-aminomethylcyclo-pent-2-en-r-1-ylmalonate, an precursor of carbocyclic homo-nucleosides, has been synthesized from the bicyclo-[2.2.1]helpt-5-ene derivative prepared by the Diels-Alder reaction of cyclopentadiene with dimethyl trifluoroacetylaminomethylenemalonate, which is a new dienophile. The synthetic method involves a novel C-C bond cleavage reaction by sodium borohydride.
Katagiri
N
N
Pharmaceutical Institute, Tohoku University, Sendai, Japan.
Makino
M
M
Nakajima
H
H
Kaneko
C
C
D001894:Borohydrides; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D008722:Methods; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
D001894:Borohydrides; D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D009705:Nucleosides; C025364:sodium borohydride