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Synthesis of the Transfer‐RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate
Author(s) -
Klepper Florian,
Jahn EvaMaria,
Hickmann Volker,
Carell Thomas
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604579
Subject(s) - allylic rearrangement , nucleoside , azide , transfer rna , chemistry , rna , stereochemistry , organic chemistry , biochemistry , catalysis , gene
Chilled out : Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0 °C, enabling a short convergent synthesis of the hypermodified transfer‐RNA nucleoside queuosine.