Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

Bing Jiang; Meng Zhao; Shu-Sen Li; Yun-He Xu; Teck-Peng Loh

doi:10.1002/anie.201710601

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

Angew Chem Int Ed Engl. 2018 Jan 8;57(2):555-559. doi: 10.1002/anie.201710601. Epub 2017 Dec 12.

Authors

Bing Jiang¹, Meng Zhao¹, Shu-Sen Li¹, Yun-He Xu¹, Teck-Peng Loh^{1

2

3}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at the Microscale iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), University of Science and Technology of China, Hefei, Anhui, 230026, China.
² Institute of Advanced Synthesis, Jiangsu National Synergetic, Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing, Jiangsu, 210009, China.
³ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637616, Singapore.

PMID: 29193496
DOI: 10.1002/anie.201710601

Abstract

A Rh^III -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.

Keywords: C−H activation; cross-coupling; homogeneous catalysis; macrocycles; rhodium.

Publication types

Research Support, Non-U.S. Gov't