Transition-Metal-Catalyzed Group Transfer Reactions for Selective C−H Bond Functionalization of Artemisinin

• DOI: 10.1021/ol071269r
• Publication Date: 2007-09-20T11:00:48Z
• Authors: Yungen Liu; Wenbo Xiao; Man-Kin Wong; Chi-Ming Che
• Keywords: Nitrene; Carbenoid; Insertion reaction; Surface Modification

Three types of novel artemisinin derivatives have been synthesized through transition-metal-catalyzed intramolecular carbenoid and nitrenoid C−H bond insertion reactions. With rhodium complexes as catalysts, lactone 11 was via carbene reaction at the C16 position in 90% yield; oxazolidinone 13 nitrene C10 87% yield based on 77% conversion; sulfamidate 14 C8 yield.