Spirocyclic restriction of nucleosides. Synthesis of the first exemplary syn-1-oxaspiro[4.4]nonanyl member

[reaction: see text] The potential benefits associated with the spirocyclic restriction of nucleosides are summarized. Following exploration of a pi-allylpalladium route to 5'-alpha- or syn-dideoxy examples, we evaluated MOM protection of the 5'-hydroxyl as being suited to the synthesis of...

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Bibliographic Details
Published in:Organic letters 2001-12, Vol.3 (25), p.4039-4041
Main Authors: Paquette, L A, Bibart, R T, Seekamp, C K, Kahane, A L
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Cyclization
Molecular Conformation
Molecular Mimicry
Molecular Structure
Nucleosides - chemical synthesis
Nucleosides - chemistry
Palladium - chemistry
Online Access:Get full text
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Summary:[reaction: see text] The potential benefits associated with the spirocyclic restriction of nucleosides are summarized. Following exploration of a pi-allylpalladium route to 5'-alpha- or syn-dideoxy examples, we evaluated MOM protection of the 5'-hydroxyl as being suited to the synthesis of the first member of this new class of nucleoside mimic.
ISSN:1523-7060
DOI:10.1021/ol010209x