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 language | English |
|---|---|
| Pages (from-to) | 500-508 |
| Number of pages | 9 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 44 |
| Issue number | 3 |
| Publication status | Published - 1996 Mar 1 |
| Externally published | Yes |
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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.