Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine.
| Autor: | Müller JM; Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King Platz 6, 20146, Hamburg, Germany., Stark CB; Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King Platz 6, 20146, Hamburg, Germany. stark@chemie.uni-hamburg.de. |
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| Jazyk: | angličtina |
| Zdroj: | Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Apr 04; Vol. 55 (15), pp. 4798-802. Date of Electronic Publication: 2016 Mar 11. |
| DOI: | 10.1002/anie.201509468 |
| Abstrakt: | A regio- and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium-catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane additive and can be switched by changing the nature of the borane. One enantiomer of the ligand is thus sufficient to prepare all possible isomers. The synthetic potential of this method was demonstrated by a short total synthesis of amauromine and its two natural diastereomers. (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
| Databáze: | MEDLINE |
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