Macrolide Synthesis through Intramolecular Oxidative Cross‐Coupling of Alkenes

A RhIII‐catalyzed intramolecular oxidative cross‐coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo‐ and stereoselectivity. This method...

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Bibliographic Details
Published in:Angewandte Chemie 2018-01, Vol.130 (2), p.564-568
Main Authors: Jiang, Bing, Zhao, Meng, Li, Shu‐Sen, Xu, Yun‐He, Loh, Teck‐Peng
Format: Article
Language:English
Subjects:
Alkenes
C-H-Aktivierung
Chemical synthesis
Chemistry
Cross coupling
Homogene Katalyse
Kreuzkupplungen
Macrocyclic compounds
Makrocyclen
Rhodium
Stereoselectivity
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Summary:A RhIII‐catalyzed intramolecular oxidative cross‐coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo‐ and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3‐conjugated diene structure. Doppelpack: Eine RhIII‐katalysierte intramolekulare oxidative Kreuzkupplung zwischen zwei Doppelbindungen kam in der Makrolid‐Synthese zum Einsatz. Unter den optimierten Bedingungen wurden Makrocyclen mit konjugiertem 1,3‐Dienmotiv in befriedigenden Ausbeuten mit ausgezeichneter Chemo‐ und Stereoselektivität erhalten.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201710601