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Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate

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  • We thank the Deutsche Forschungsgemeinschaft (DFG), the Volkswagen Foundation (Priority Program: Conformational Control of Biomolecular Function), the EU Marie Curie Training Mobility Program (CLUSTOXDNA), and the Fonds der Chemischen Industrie for generous financial support of this research.

Abstract

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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.

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