Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B

Beschreibung

In his thesis, Xiao-yu Sun conducts the first total synthesis of all possible stereoisomers of plakortide E and also confirms the absolute configuration of natural plakortide E. Xiao-yu Sun subsequently converts Plakortide E methyl ester to plakortone B in a biomimetic conversion. Construction and functionalization of cyclic peroxides are notoriously difficult due to the very low O-O bond dissociation energy. Plaktoride E is isolated from the Jamaican marine sponge platorits halichondrioides and contains a five-membered peroxide ring, with oxygen atoms linked to tertiary C4 and C6 centers. The methodology used for synthesizing highly substituted cyclic peroxides is novel and useful, and not only extends the field of Pd-catalyzed reactions, but also provides a convenient synthetic approach for the preparation of the 1,2-dioxolanes series. Plakortide E and plakortone B are bioactive, which means that the synthetic studies on them and their analogs are pivotal in drug discovery.
In his thesis, Xiaoyu Sun conducts the first total synthesis of all possible stereoisomers of plakortide E and also confirms the absolute configuration of natural plakortide E. Xiaoyu Sun subsequently converts Plakortide E methyl ester to plakortone B in a biomimetic conversion. Construction and functionalization of cyclic peroxides are notoriously difficult due to the very low O-O bond dissociation energy. Plaktoride E is isolated from the Jamaican marine sponge platorits halichondrioides and contains a five-membered peroxide ring, with oxygen atoms linked to tertiary C4 and C6 centers. The methodology used for synthesizing highly substituted cyclic peroxides is novel and useful, and not only extends the field of Pd-catalyzed reactions, but also provides a convenient synthetic approach for the preparation of the 1,2-dioxolanes series. Plakortide E and plakortone B are bioactive, which means that the synthetic studies on them and their analogs are pivotal in drug discovery.
Nominated by the Chinese University of Hong Kong as an outstanding PhD thesis Novel and useful methodology for synthesizing highly substituted cyclic peroxides Extends the field of Pd-catalyzed reactions Includes supplementary material: sn.pub/extras

Autor*in

Xiao-Yu Sun

Themen in »Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B«

Springer Thesis Prize biomimetic synthesis of plakortone B cascade reaction lipase-catalyzed kinetic resolution metal-halogen exchange on cyclic peroxides total synthesis of plakortide E

Stimmen zu »Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B«

Details

Link teilen