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Stereoselective Synthesis of Highly Functionalized Hydroindoles as Building Blocks for Rostratins B–D and Synthesis of the Pentacyclic Core of Rostratin C |
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| Authors: | Dr. Sabilla Zhong Paul F. Sauter Dr. Martin Nieger Prof. Dr. Stefan Bräse |
| Affiliation: | 1. Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz‐Haber‐Weg 6, 76131 Karlsruhe (Germany);2. Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P. O. Box 55, 00014 (Finland);3. Karlsruhe Institute of Technology, Institute of Toxicology and Genetics, Hermann‐von‐Helmholtz‐Platz 1, 76344 Eggenstein‐Leopoldshafen (Germany) |
| Abstract: | The stereoselective synthesis of a variety of functionalized hydroindoles suitable as building blocks for thiodiketopiperazine natural products such as rostratins B–D is reported. The key precursor for all transformations is a previously reported hexahydroindole compound. All functional groups were installed with the desired stereochemistry and the feasibility of the synthetic strategy was exemplified by dimerization of two hydroindole units to form the pentacyclic C2‐symmetric scaffold of rostratin C. |
| Keywords: | dimerization hydroindoles natural products nitrogen heterocycles polycycles |