Synthesis of highly dehydrogenated oxoerythrinan alkaloids, erytharbine and crystamidine

Y. Tsuda, S. Hosoi, F. Kiuchi, Fumiyuki Kiuchi, R. Yamamoto, T. Sano

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation of 3,8-dioxoerythrinan-1(6)-enes in dioxane gave the ring B dehydrogenated products, the 1,6-dienones, while oxidation in benzene gave the fully dehydrogenated products, the 1,6,10-trienones. The same trienones were obtained by DDQ oxidation of the 1,6-dienones in benzene. On the contrary, oxidation of the isomeric enone, 3,8-dioxoerythrinan-1-ene, in either dioxane or benzene gave the ring C dehydrogenated product, the 1,10-dienone. The 1,6,10-trienones were transformed to the highly dehydrogenated 8-oxoerythrinan alkaloids, erytharbine and crystamidine, in racemic forms.

Original languageEnglish
Pages (from-to)965-967
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number5
Publication statusPublished - 1993
Externally publishedYes

Fingerprint

Benzene
Alkaloids
Oxidation
1,4-dioxane

Keywords

  • crystamidine
  • DDQ
  • dehydrogenation
  • erytharbine
  • Erythrina alkaloid
  • total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Synthesis of highly dehydrogenated oxoerythrinan alkaloids, erytharbine and crystamidine. / Tsuda, Y.; Hosoi, S.; Kiuchi, F.; Kiuchi, Fumiyuki; Yamamoto, R.; Sano, T.

In: Chemical and Pharmaceutical Bulletin, Vol. 41, No. 5, 1993, p. 965-967.

Research output: Contribution to journalArticle

Tsuda, Y, Hosoi, S, Kiuchi, F, Kiuchi, F, Yamamoto, R & Sano, T 1993, 'Synthesis of highly dehydrogenated oxoerythrinan alkaloids, erytharbine and crystamidine', Chemical and Pharmaceutical Bulletin, vol. 41, no. 5, pp. 965-967.
Tsuda, Y. ; Hosoi, S. ; Kiuchi, F. ; Kiuchi, Fumiyuki ; Yamamoto, R. ; Sano, T. / Synthesis of highly dehydrogenated oxoerythrinan alkaloids, erytharbine and crystamidine. In: Chemical and Pharmaceutical Bulletin. 1993 ; Vol. 41, No. 5. pp. 965-967.
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AU - Hosoi, S.

AU - Kiuchi, F.

AU - Kiuchi, Fumiyuki

AU - Yamamoto, R.

AU - Sano, T.

PY - 1993

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N2 - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation of 3,8-dioxoerythrinan-1(6)-enes in dioxane gave the ring B dehydrogenated products, the 1,6-dienones, while oxidation in benzene gave the fully dehydrogenated products, the 1,6,10-trienones. The same trienones were obtained by DDQ oxidation of the 1,6-dienones in benzene. On the contrary, oxidation of the isomeric enone, 3,8-dioxoerythrinan-1-ene, in either dioxane or benzene gave the ring C dehydrogenated product, the 1,10-dienone. The 1,6,10-trienones were transformed to the highly dehydrogenated 8-oxoerythrinan alkaloids, erytharbine and crystamidine, in racemic forms.

AB - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation of 3,8-dioxoerythrinan-1(6)-enes in dioxane gave the ring B dehydrogenated products, the 1,6-dienones, while oxidation in benzene gave the fully dehydrogenated products, the 1,6,10-trienones. The same trienones were obtained by DDQ oxidation of the 1,6-dienones in benzene. On the contrary, oxidation of the isomeric enone, 3,8-dioxoerythrinan-1-ene, in either dioxane or benzene gave the ring C dehydrogenated product, the 1,10-dienone. The 1,6,10-trienones were transformed to the highly dehydrogenated 8-oxoerythrinan alkaloids, erytharbine and crystamidine, in racemic forms.

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