Macrolide Synthesis through Intramolecular Oxidative Cross‐Coupling of Alkenes

• Published in: Angewandte Chemie International Edition Vol. 57; no. 2; pp. 555 - 559
• Main Authors: Jiang, Bing, Zhao, Meng, Li, Shu‐Sen, Xu, Yun‐He, Loh, Teck‐Peng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.01.2018; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkenes; Antibiotics; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Cross coupling; C−H activation; homogeneous catalysis; macrocycles; Macrocyclic compounds; Physical Sciences; rhodium; Science & Technology; Stereoselectivity; ORGANOBORON COMPOUNDS; CATALYSIS; NUCLEOPHILIC FLUORINATION; LEWIS-ACID; FLUORIDE-ION DETECTION; COMPLEXES; REACTIVITY; RECEPTOR; C-H activation; homogeneous catalysis; macrocycles; cross-coupling; ANION RECOGNITION; BOND; rhodium; C−H activation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201710601

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. Two pair: A RhIII‐catalyzed intramolecular oxidative cross‐coupling between double bonds for the synthesis of macrolides is described. Under the optimized conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo‐ and stereoselectivity. This provides efficient access to macrocyclic compounds containing 1,3‐conjugated dienes.