Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine

Yoshisuke Tsuda, Takeshi Ohshima, Shinzo Hosoi, Satomi Kaneuchi, Fumiyuki Kiuchi, Jun Toda, Takehiro Sano

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Total syntheses of two homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyclobutane derivative, which was converted to a homoerythrinan derivative by utilizing a TBAF-induced 1,3-anionic rearrangement. The product was transformed into the title alkaloids in several steps.

Original languageEnglish
Pages (from-to)500-508
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume44
Issue number3
Publication statusPublished - 1996 Mar 1
Externally publishedYes

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Keywords

  • 1,3-anionio rearrangement
  • 3-epischelhammericine, [2 + 2]photo-cyclo-addition
  • Homoerythrinan alkaloid
  • Schelhammericine
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Tsuda, Y., Ohshima, T., Hosoi, S., Kaneuchi, S., Kiuchi, F., Toda, J., & Sano, T. (1996). Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine. Chemical and Pharmaceutical Bulletin, 44(3), 500-508.