A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum

Naoto Yamasaki, Ikumi Iwasaki, Kazu Sakumi, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Masataka Nakahara, Shuhei Higashibayashi, Takeshi Sugai, Hiroshi Imagawa, Miwa Kubo, Yoshiyasu Fukuyama, Satoshi Ōmura, Hirofumi Yamamoto

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)5555-5563
Number of pages9
JournalChemistry - A European Journal
Volume27
Issue number17
DOIs
Publication statusPublished - 2021 Mar 22

Keywords

  • Diels–Alder reactions
  • antimalarial drugs
  • dehydroantofine
  • density functional calculations
  • pi interactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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