High pressure mediated Diels-Alder reaction using 2-iminomalonates as dienophiles: novel synthesis of carbocyclic nucleosides.
9-[c-4-(1,2-Dihydroxyethyl)cyclopent-2-en-r-1-yl]-9H-adenine , an isomer of BCA, has been synthesized from Diels-Alder adducts prepared by the reaction of 2-iminomalonates with cyclopentadiene under high pressure. The synthetic method involves a novel C-N bond cleavage reaction by NaBH4-K2CO3 (RRA reaction conditions) and has wide applicability for the synthesis of various carbocyclic nucleosides.
Katagiri
N
N
Pharmaceutical Institute, Tohoku University, Sendai, Japan.
Kurimoto
A
A
Kitano
K
K
Nochi
H
H
Sato
H
H
Kaneko
C
C
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D008314:Malonates / Q000737:chemistry*; D011312:Pressure
D003517:Cyclopentanes; D008314:Malonates; C079757:9-(4-(1,2-dihydroxyethyl)cyclopent-2-en-1-yl)-9H-adenine; D000225:Adenine