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Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B (Springer Theses)

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en Limba Engleză Hardback – 16 Jan 2012
This thesis presents the first total synthesis of all possible stereoisomers of plakortide E and also confirms the absolute configuration of natural plakortide E. It also details a biomimetic method for converting Plakortide E methyl ester to plakortone B.
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Specificații

ISBN-13: 9783642271946
ISBN-10: 3642271944
Pagini: 290
Ilustrații: 303 schwarz-weiße und 5 farbige Abbildungen
Dimensiuni: 155 x 235 x 23 mm
Greutate: 0.52 kg
Ediția: 2012
Editura: Springer Berlin, Heidelberg
Colecția Springer
Seria Springer Theses

Locul publicării: Berlin, Heidelberg, Germany

Public țintă

Research

Caracteristici

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

Cuprins

Introduction.- Results and Discussion.- Conclusion.- Experimental Section.- References.- Appendix I.- Appendix II.

Textul de pe ultima copertă

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.