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Synthesis of a novel conformationally locked carbocyclic nucleoside ring system.

ABSTRACT: [reaction: see text] A fast and efficient synthetic route to novel Northern locked carbocyclic nucleosides (as precursors of carbocyclic locked nucleic acids or cLNAs) is described. The target nucleoside with a oxabicyclo[2.2.1]heptane ring system was prepared from a simple starting material, diethyl malonate. Ring closure by intramolecular O-alkylation provided the target ring system as the major isomer over the [3.2.0] oxetane system. The adenine moiety was introduced through a reactive triflate after inversion of the stereochemistry of the corresponding alcohol by oxidation and reduction.

SUBMITTER: Kim HS

PROVIDER: S-EPMC3153471 | biostudies-literature | 2003 May

REPOSITORIES: biostudies-literature

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Synthesis of a novel conformationally locked carbocyclic nucleoside ring system.

Kim Hak Sung HS Jacobson Kenneth A KA

Organic letters 20030501 10

[reaction: see text] A fast and efficient synthetic route to novel Northern locked carbocyclic nucleosides (as precursors of carbocyclic locked nucleic acids or cLNAs) is described. The target nucleoside with a oxabicyclo[2.2.1]heptane ring system was prepared from a simple starting material, diethyl malonate. Ring closure by intramolecular O-alkylation provided the target ring system as the major isomer over the [3.2.0] oxetane system. The adenine moiety was introduced through a reactive trifla ...[more]

PMID: 12735747

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