title: High pressure mediated Diels-Alder reaction using 2-iminomalonates as dienophiles: novel synthesis of carbocyclic nucleosides.
abstract: 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.
authors.affiliation: Pharmaceutical Institute, Tohoku University, Sendai, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Katagiri
authors.forename: A
authors.initials: A
authors.lastname: Kurimoto
authors.forename: K
authors.initials: K
authors.lastname: Kitano
authors.forename: H
authors.initials: H
authors.lastname: Nochi
authors.forename: H
authors.initials: H
authors.lastname: Sato
authors.forename: C
authors.initials: C
authors.lastname: Kaneko
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D008314:Malonates / Q000737:chemistry*; D011312:Pressure
chemical_list: D003517:Cyclopentanes; D008314:Malonates; C079757:9-(4-(1,2-dihydroxyethyl)cyclopent-2-en-1-yl)-9H-adenine; D000225:Adenine