High pressure mediated Diels-Alder reaction using 2-iminomalonates as dienophiles: novel synthesis of carbocyclic nucleosides.

N. Katagiri, A. Kurimoto, K. Kitano, H. Nochi, H. Sato, C. Kaneko

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)83-84
Number of pages2
JournalNucleic acids symposium series
Issue number27
Publication statusPublished - 1992

ASJC Scopus subject areas

  • Medicine(all)

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