Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B
Seiten
2014
|
2012
Springer Berlin (Verlag)
978-3-642-44211-7 (ISBN)
Springer Berlin (Verlag)
978-3-642-44211-7 (ISBN)
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.
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.
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.
Introduction.- Results and Discussion.- Conclusion.- Experimental Section.- References.- Appendix I.- Appendix II.
Erscheint lt. Verlag | 22.2.2014 |
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Reihe/Serie | Springer Theses |
Zusatzinfo | XIV, 222 p. |
Verlagsort | Berlin |
Sprache | englisch |
Maße | 155 x 235 mm |
Gewicht | 364 g |
Themenwelt | Medizin / Pharmazie ► Pharmazie |
Naturwissenschaften ► Biologie ► Biochemie | |
Naturwissenschaften ► Chemie ► Organische Chemie | |
Naturwissenschaften ► Chemie ► Physikalische Chemie | |
Schlagworte | biomimetic synthesis of plakortone B • cascade reaction • lipase-catalyzed kinetic resolution • metal-halogen exchange on cyclic peroxides • Springer Thesis Prize • total synthesis of plakortide E |
ISBN-10 | 3-642-44211-0 / 3642442110 |
ISBN-13 | 978-3-642-44211-7 / 9783642442117 |
Zustand | Neuware |
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