Concise Synthesis of (+)‐[13C4]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion
| Autor: | Armen Zakarian, Jacob J. Lacharity, Karen Y. Chen, Artur K. Mailyan |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Enantioselective synthesis Iminium Total synthesis General Medicine General Chemistry 010402 general chemistry 01 natural sciences C-4 Catalysis 0104 chemical sciences Ion law.invention Kinetic resolution Computational chemistry law Chirality (chemistry) Racemization |
| Zdroj: | Angewandte Chemie International Edition. 59:11364-11368 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202004464 |
| Popis: | An asymmetric total synthesis of [13 C4 ]-anatoxin-a ([13 C4 ]-1) has been developed from commercially available ethyl [13 C4 ]-acetoacetate ([13 C4 ]-15). The unique requirements associated with isotope incorporation inspired a new, robust, and highly scalable route, providing access to 0.110 g of this internal standard for use in the detection and precise quantification of anatoxin-a in freshwater. A highlight of the synthesis is a method that leverages a cyclic iminium ion racemization to achieve dynamic kinetic resolution in an enantioselective Morita-Baylis-Hillman (MBH) cyclization. |
| Databáze: | OpenAIRE |
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