Total Synthesis of Tagetitoxin
| Autor: | Chi He, Phil S. Baran, Thomas P. Stratton, David Kossler, Hang Chu, Kelly J. Eberle, Dillon T. Flood |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Natural product
Molecular Structure Stereochemistry Extramural Absolute configuration Total synthesis Stereoisomerism General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Catalysis Article 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Organophosphorus Compounds chemistry Furan Dicarboxylic Acids Tagetitoxin |
| Zdroj: | J Am Chem Soc |
| Popis: | The intriguing structure of tagetitoxin (1), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, and P(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the absolute configuration of the natural product could be assigned using a bioassay on (+)-1 and (-)-1. |
| Databáze: | OpenAIRE |
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