Synthesis of Highly Dehydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine1,2)

Yoshisuke Tsuda, Jun Toda, Shinzo Hosoi, Fumiyuki Kiuchi, Ryuzo Yamamoto, Takehiro 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-l(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 bezene. 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
DOIs
Publication statusPublished - 1993 Jan 1
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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