Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom