Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0 x 10-7 M). (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3145-3148
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number17
DOIs
Publication statusPublished - Apr 22 2000

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals'. Together they form a unique fingerprint.

Cite this