Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol
| Autor: | Brian M. Stoltz, Jeffrey T. Bagdanoff, Douglas C. Behenna, Jennifer L. Stockdill |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Zoanthenol Organic Chemistry Synthon Glycidol Enantioselective synthesis Caprolactam Alkyne 010402 general chemistry Ring (chemistry) 01 natural sciences Article 0104 chemical sciences chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Enone |
| Popis: | The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this synthetic approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting group strategy led to the modification of this approach beginning with (±)-glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero-Diels-Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition to the corresponding enone synthon. Addition of a model alkyne provides support for the late-stage addition of a hindered alkyne into the caprolactam building block. |
| Databáze: | OpenAIRE |
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