Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone
| Autor: | Henry P. Pepper, Stephen J. Tulip, Jonathan H. George, Yuji Nakano |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Biological Products
Molecular Structure 010405 organic chemistry Stereochemistry Chemistry Chemical structure Monoterpene Organic Chemistry Enantioselective synthesis Absolute configuration Total synthesis Stereoisomerism 010402 general chemistry 01 natural sciences Combinatorial chemistry Radical cyclization 0104 chemical sciences Benzophenones Biomimetics Cyclization Molecule Polycyclic Compounds Oxidation-Reduction |
| Zdroj: | The Journal of organic chemistry. 79(6) |
| ISSN: | 1520-6904 |
| Popis: | A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|