A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum.
Naoto YamasakiIkumi IwasakiKazu SakumiRei HokariAki IshiyamaMasato IwatsukiMasataka NakaharaShuhei HigashibayashiTakeshi SugaiHiroshi ImagawaMiwa KuboYoshiyasu FukuyamaSatoshi ŌmuraHirofumi YamamotoPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2021)
The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels-Alder reaction of easily accessible 3,5-dichloro-2H-1,4-oxazin-2-one with 14 a as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine-resistant Plasmodium falciparum.
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