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A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine‐Resistant Plasmodium falciparum
Author(s) -
Yamasaki Naoto,
Iwasaki Ikumi,
Sakumi Kazu,
Hokari Rei,
Ishiyama Aki,
Iwatsuki Masato,
Nakahara Masataka,
Higashibayashi Shuhei,
Sugai Takeshi,
Imagawa Hiroshi,
Kubo Miwa,
Fukuyama Yoshiyasu,
Ōmura Satoshi,
Yamamoto Hirofumi
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100032
Subject(s) - plasmodium falciparum , chloroquine , regioselectivity , antimalarial agent , chemistry , stereochemistry , plasmodium (life cycle) , combinatorial chemistry , malaria , biology , biochemistry , parasite hosting , computer science , immunology , catalysis , world wide web
The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5‐dichloro‐2 H ‐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 .