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- Title
First Total Synthesis of the Cytotoxic Carbazole Alkaloid Excavatine-A and Regioselective Annulation to Pyrano[2,3-a]carbazoles and [1,4]Oxazepino[2,3,4-jk]carbazoles.
- Authors
Brütting, Christian; Kataeva, Olga; Schmidt, Arndt W.; Knölker, Hans‐Joachim
- Abstract
We describe the first total synthesis of the cytotoxic carbazole alkaloid excavatine-A. The carbazole framework was constructed through double C-H bond activation of a diarylamine by using our palladium(II)-catalyzed oxidative cyclization. Treatment of the intermediate 8-hydroxycarbazoles with prenal and different additives led either to pyrano[2,3-a]carbazoles or to [1,4]oxazepino[2,3,4-jk]carbazoles. The pyran annulation was investigated to determine the influence of substitution pattern, additives, and reaction time on the selectivity.
- Subjects
ALKALOID synthesis; CYTOTOXIC T cells; ANNULATION; CARBAZOLE; PYRAN synthesis
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 22, p3288
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700515