Chhor, Rakeshwar B. and Nosse, Bernd and Sörgel, Sebastian and Böhm, Claudius and Seitz, Michael and Reiser, Oliver (2003) Enantioselective Synthesis of Paraconic Acids. Chemistry - A European Journal 9 (1), pp. 260-270.
Full text not available from this repository.
Other URL: http://dx.doi.org/10.1002/chem.200390019
The development of a new method for the enantioselective synthesis of disubstituted -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.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser|
|Keywords:||asymmetric synthesis; lactones; metathesis; natural products; total synthesis|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Owner:||Helge Knüttel (ADMIN)|
|Deposited On:||04 Sep 2006|
|Last Modified:||05 Aug 2009 13:22|