Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH

Takahiro Tokuyasu, Shigeki Kunikawa, Manabu Abe, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Khurshida Begum, Yusuke Wataya

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Abstract

Co(II)-catalyzed peroxidation of dienes including (S)-limonene in the presence of molecular oxygen and triethylsilane provided in each case the corresponding 2,3-dioxabicyclo[3.3.1]nonane derivatives via the intramolecular cyclization of the unsaturated peroxy radical intermediates. The product composition was remarkably influenced by the structure of the dienes, the nature of the solvents, and the concentration of the substrates and the catalyst. Some of the yingzhaosu A analogues obtained in this study showed notable antimalarial activities in vitro.

Original languageEnglish
Pages (from-to)7361-7367
Number of pages7
JournalJournal of Organic Chemistry
Volume68
Issue number19
Publication statusPublished - Sep 19 2003

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tokuyasu, T., Kunikawa, S., Abe, M., Masuyama, A., Nojima, M., Kim, H. S., Begum, K., & Wataya, Y. (2003). Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH. Journal of Organic Chemistry, 68(19), 7361-7367.