| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Total Synthesis of Sordaricin
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important classof antifungal compounds, is described. Two approaches were explored, the first of which utilized apossible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton ofthe target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but alsosignificant quantities of the undesired regioisomer iso-30. An investigation into the reasons forthe difference in regioselectivity between these two reactions revealed the intervention of acycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30.Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stableof the two regioisomers.
|
| article type
| |
| is part of this journal
| |
