PhD ceremony Mr. Y. Huang: Copper-catalyzed asymmetric allylic alkylation and asymmetric conjugate addition in natural product synthesis

PhD ceremony: Mr. Y. Huang, 12.45 uur, Academiegebouw, Broerstraat 5, Groningen

Dissertation: Copper-catalyzed asymmetric allylic alkylation and asymmetric conjugate addition in natural product synthesis

Promotor(s): prof. B.L. Feringa, prof. A.J. Minnaard

Faculty: Mathematics and Natural Sciences

Catalytic asymmetric C-C bond forming reactions using organometallics are among the most important organic transformations. The AAA (asymmetric allylic alkylation) and ACA (asymmetric conjugate addition) are particular versatile in enantioselective C-C bond forming reactions. Especially applying ACA, the intermediate enolate formed could be further functionalized by reaction with other electrophiles (one-pot transformations). These transformations are frequently applied in the synthesis of complex biologically active molecules. In this thesis, copper-catalyzed hetero AAA and ACA are described in the total synthesis of several biologically active molecules (Lasiodiplodin, Rasfonin and Zearalenone). A second part of this thesis aims at the development of a novel catalytic asymmetric route towards skipped dienes with a methyl substituted central stereogenic carbon using copper-catalyzed AAA and its application in the total synthesis of natural product, Phorbasin B.