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
Externally publishedYes

Fingerprint

Alkaloids
Cyclobutanes
Derivatives

Keywords

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

ASJC Scopus subject areas

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

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.

Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine. / Tsuda, Yoshisuke; Ohshima, Takeshi; Hosoi, Shinzo; Kaneuchi, Satomi; Kiuchi, Fumiyuki; Toda, Jun; Sano, Takehiro.

In: Chemical and Pharmaceutical Bulletin, Vol. 44, No. 3, 03.1996, p. 500-508.

Research output: Contribution to journalArticle

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, vol. 44, no. 3, pp. 500-508.
Tsuda, Yoshisuke ; Ohshima, Takeshi ; Hosoi, Shinzo ; Kaneuchi, Satomi ; Kiuchi, Fumiyuki ; Toda, Jun ; Sano, Takehiro. / Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine. In: Chemical and Pharmaceutical Bulletin. 1996 ; Vol. 44, No. 3. pp. 500-508.
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