Chhor, Rakeshwar B. and Nosse, Bernd and Soergel, Sebastian and Boehm, Claudius and Seitz, Michael and Reiser, Oliver (2003) Enantioselective synthesis of paraconic acids. CHEMISTRY-A EUROPEAN JOURNAL, 9 (1). pp. 260-270. ISSN 0947-6539
Full text not available from this repository.Abstract
The development of a new method for the enantioselective synthesis of disubstituted gamma-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I) -catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DL-PROTOLICHESTERINIC ACID; SUBSTITUTED GAMMA-BUTYROLACTONES; ALPHA-METHYLENE BUTYROLACTONES; CHIRAL HOMOENOLATE REAGENTS; OLEFIN CROSS-METATHESIS; STEREOSELECTIVE-SYNTHESIS; (-)-ROCCELLARIC ACID; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; asymmetric synthesis; lactones; metathesis; natural products; total synthesis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Petra Gürster |
| Date Deposited: | 23 Jun 2021 10:35 |
| Last Modified: | 23 Jun 2021 10:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/39365 |
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