Further Investigation of the Intermolecular Diels–Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids
| Autor: | Jonathan C. Perkins, Robert D. Pike, Xiye Wang, Jonathan R. Scheerer |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Aza Compounds
Cycloaddition Reaction Molecular Structure Bicyclic molecule 010405 organic chemistry Organic Chemistry Intermolecular force Convergent synthesis Maleic anhydride 010402 general chemistry Ring (chemistry) 01 natural sciences Article Piperazines Cycloaddition 0104 chemical sciences Bridged Bicyclo Compounds chemistry.chemical_compound Alkaloids chemistry Organic chemistry Spiro Compounds Brevianamide Reactivity (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 82:13656-13662 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.7b02403 |
| Popis: | The convergent synthesis of bicyclo[2.2.2]diazaoctane structures using an intermolecular Diels−Alder cyclo-addition between a pyrazinone and commercially available fumarate or maleate precursors is reported. High reactivity and stereoselection is observed with both dienophile substrates. Structure validation was achieved by conversion of cycloadducts into known [2.2.2]diazabicyclic compounds or into crystalline derivatives suitable for X-ray analysis. The cycloadduct derived from reaction of pyrazinone and maleic anhydride underwent selective anhydride ring opening and intersected an established precursor in the synthesis of brevianamide B. |
| Databáze: | OpenAIRE |
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