Dobler, Daniel and Reiser, Oliver (2016) Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one. JOURNAL OF ORGANIC CHEMISTRY, 81 (21). pp. 10357-10365. ISSN 0022-3263,
Full text not available from this repository. (Request a copy)Abstract
An atom-economic reaction sequence to 6-substituted 2-pyrones was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, and aldehydes, utilizing a thermal rearrangement of cyclopentadienone epoxides as key step. Derivatives bearing a hydroxyalkyl side chain could be enzymatically resolved, providing access to enantiomerically pure 2-pyrones, or converted to alkenyl-substituted 2-pyrones such as naturally occurring sibirinone, (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(hept-l-en-l-yl)-2H-pyran-2-one.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | NOVO ASYMMETRIC-SYNTHESIS; ALPHA-PYRONES; COUPLING REACTIONS; ORGANIC-SYNTHESIS; CYCLOPENTADIENONE; THERMOLYSIS; 4-HYDROXYCYCLOPENT-2-EN-1-ONE; TRICYCLODECADIENONE; VERSATILE; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Apr 2019 11:49 |
| Last Modified: | 12 Apr 2019 11:49 |
| URI: | https://pred.uni-regensburg.de/id/eprint/3964 |
Actions (login required)
 |
View Item |
