Abstract
The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.
Original language | English (US) |
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Pages (from-to) | 3690-3693 |
Number of pages | 4 |
Journal | Tetrahedron |
Volume | 71 |
Issue number | 22 |
DOIs | |
State | Published - Jun 3 2015 |
Keywords
- Cyclization
- Imidazole
- Pyrrole
- Radical
- Single-electron transfer
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry