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