Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin.
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 synthesized via carbene insertion reaction at the C16 position in 90% yield; oxazolidinone 13 was synthesized via nitrene insertion reaction at the C10 position in 87% yield based on 77% conversion; and sulfamidate 14 was synthesized via nitrene insertion reaction at the C8 position in 87% yield.
Liu
Yungen
Y
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Xiao
Wenbo
W
Wong
Man-Kin
MK
Che
Chi-Ming
CM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D028561:Transition Elements / Q000737:chemistry
D000970:Antineoplastic Agents; D037621:Artemisinins; D028561:Transition Elements; D012238:Rhodium