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Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis

✍ Scribed by Ok Hyun Ko; Joon Hee Hong

Book ID: 104251738
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 72 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01384-9

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✦ Synopsis

Very efficient synthetic route to novel 4%a-C-hydroxymethyl branched carbocyclic nucleosides was described. The stereocontrolled synthesis of target nucleosides was successfully achieved by Johnson orthoester-Claisen rearrangement, ring-closing metathesis (RCM) starting from a simple acyclic precursor 1,3-dihydoxy acetone 1. Nucleosidic bases (adenine and cytosine) were coupled by Pd(0)-catalyzed allylic alkylation in a highly regiocontrolled manner.

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