Biomimetic synthesis of antimalarial naphthoquinones

Jeremiah P. Malerich, Thomas J. Maimone, Gregory I. Elliott, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The total synthesis of naphthoquinone natural products isolated from the Bignoniaceae plant family is described. Pinnatal, isopinnatal, sterekunthals A and B, pyranokunthones A and B, and anthrakunthone have been prepared along the lines of a biosynthetic proposal involving pericyclic reactions as key steps. The first case of catalysis in oxa 6π electrocyclizations is reported.

Original languageEnglish (US)
Pages (from-to)6276-6283
Number of pages8
JournalJournal of the American Chemical Society
Volume127
Issue number17
DOIs
StatePublished - May 4 2005

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Bignoniaceae
Naphthoquinones
Biomimetics
Antimalarials
Biological Products
Catalysis
isopinnatal
sterekunthal A
pinnatal

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Malerich, J. P., Maimone, T. J., Elliott, G. I., & Trauner, D. (2005). Biomimetic synthesis of antimalarial naphthoquinones. Journal of the American Chemical Society, 127(17), 6276-6283. https://doi.org/10.1021/ja050092y

Biomimetic synthesis of antimalarial naphthoquinones. / Malerich, Jeremiah P.; Maimone, Thomas J.; Elliott, Gregory I.; Trauner, Dirk.

In: Journal of the American Chemical Society, Vol. 127, No. 17, 04.05.2005, p. 6276-6283.

Research output: Contribution to journalArticle

Malerich, JP, Maimone, TJ, Elliott, GI & Trauner, D 2005, 'Biomimetic synthesis of antimalarial naphthoquinones', Journal of the American Chemical Society, vol. 127, no. 17, pp. 6276-6283. https://doi.org/10.1021/ja050092y
Malerich, Jeremiah P. ; Maimone, Thomas J. ; Elliott, Gregory I. ; Trauner, Dirk. / Biomimetic synthesis of antimalarial naphthoquinones. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 17. pp. 6276-6283.
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