An unusual intramolecular hetero-Diels-Alder cycloaddition
| Autor: | Robert F. Keyes, Kent D. Stewart, Eric J. Stoner, Rodger F. Henry, Michael S. Allen, L. Steven Hollis, Ian Marsden, Sandeep G. Shiroor, Tamara C. Rehm, Niru B. Soni, Alan Christesen |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Reaction mechanism
Ketolides Aqueous solution Molecular model Intramolecular reaction Molecular Structure Chemistry Stereochemistry Organic Chemistry Molecular Conformation Stereoisomerism Crystallography X-Ray Cycloaddition Catalysis Adduct Erythromycin Cyclization Intramolecular force Cis–trans isomerism |
| Zdroj: | The Journal of organic chemistry. 70(8) |
| ISSN: | 0022-3263 |
| Popis: | A new reaction of erythronolides, an intramolecular hetero-Diels-Alder, has been discovered. Heated aqueous alcoholic solutions of ABT-773 (1) and its cis isomer (3) convert slowly to cycloadducts 2 and 4, respectively. Optimal reaction conditions, mechanistic studies supported by molecular modeling, and biological activity data are reported. Single-crystal X-ray structures for both adducts 2 and 4 have been obtained. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|