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Synthesis 2013; 45(10): 1300-1311
DOI: 10.1055/s-0032-1317810
DOI: 10.1055/s-0032-1317810
feature article
Assembly of the Nosiheptide A-Ring: A Fruitful Lesson
Further Information
Publication History
Received: 15 February 2013
Accepted after revision: 21 March 2013
Publication Date:
25 April 2013 (online)
Abstract
The synthesis of a 28-membered thiopeptide macrocycle is described. Key steps are mild aza-Wittig thiazole ring closures, a scandium(III)-mediated regioselective ester hydrolysis, and a highly efficient macrolactam formation with its 3-hydroxypyridine nucleus orthogonally protected.
Key words
antibiotics - aza-Wittig reaction - heterocycles - natural products - macrocyclization - thiopeptides.Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
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Reviews:
Thiopeptide total synthesis work after 2009:
Synthesis of indole fragments:
Synthesis of thiazole fragments:
Synthesis of the 3-hydroxypyridine core: