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

Abstract

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z604579_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.