Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade
| Autor: | Clayton H. Heathcock, Grier A. Wallace |
|---|---|
| Rok vydání: | 2000 |
| Předmět: |
Molecular Structure
biology Stereochemistry Chemistry Alkaloid Organic Chemistry biology.organism_classification Daphniphyllum macropodum Trees Structure-Activity Relationship Alkaloids Cycadopsida Cascade reaction Cascade Intramolecular force Structure–activity relationship Molecule Indicators and Reagents Daphniphyllum |
| Zdroj: | The Journal of Organic Chemistry. 66:450-454 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo001145r |
| Popis: | The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 2-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade. |
| Databáze: | OpenAIRE |
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