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Beiträge zu den Totalsynthesen der natürlichen 3-Acyltetramsäuren Discodermid, Methiosetin und TA-289

URN to cite this document: urn:nbn:de:bvb:703-epub-3342-6

Title data

Winterer, Markus:
Beiträge zu den Totalsynthesen der natürlichen 3-Acyltetramsäuren Discodermid, Methiosetin und TA-289.
Bayreuth , 2017 . - 186 P.
( Doctoral thesis, 2017 , University of Bayreuth, Faculty of Biology, Chemistry and Earth Sciences)

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Project information

Project financing: Deutsche Forschungsgemeinschaft

Abstract

Diese Arbeit beschäftigt sich mit den Totalsynthesen der natürlichen 3-Acyltetramsäuren Discodermid, Methiosetin und TA-289. 3-Acyltetramsäuren liegen aufgrund ihrer hohen Bioaktivität im Fokus vieler Naturstoffchemiker. Es sollten für die Totalsynthesen in dieser Arbeit neue Methoden zum Aufbau von Makrolactam- bzw. Decalinoyl-Tetramsäuren evaluiert werden. So wurde der Zugang zu Discodermid unter dreimaliger Verwendung von Ph3PCCO untersucht. Methiosetin konnte unter zweimaligem Einsatz von Ph3PCCO und über eine substratinduzierte intramolekulare Diels-Alder-Reaktion auf später Stufe erzeugt werden. TA-289 wurde über eine für Decalinoyl-Tetramsäuren ebenso noch nicht verwendete BF3-Etherat-vermittelte Jones-Acylierung aufgebaut.

Abstract in another language

This work deals with the total syntheses of the naturally occurring 3-acyltetramic acids discodermide, methiosetin and TA-289. Due to their frequently observed high bioactivity, 3-acyltetramic acids are the focus of many natural product chemists. In the present thesis methods for the construction of macrolactam or decalinoyl tetramic acids should be evaluated. Thus, the access to discodermid was examined under three-time use of Ph3PCCO. Methiosetin could be generated with twice employment of Ph3PCCO via a substrate-induced intramolecular Diels-Alder reaction on a later stage. TA-289 was synthesized via a BF3-etherate mediated Jones acylation that has not yet been used for decalinoyl tetramic acids.

Further data

Item Type: Doctoral thesis (No information)
Keywords: tetramic acids; natural products; total synthesis; discodermide; methiosetin; TA-289; late-stage-Diels Alder reaction
DDC Subjects: 500 Science > 500 Natural sciences
500 Science > 540 Chemistry
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I > Chair Organic Chemistry I - Univ.-Prof. Dr. Rainer Schobert
Graduate Schools > University of Bayreuth Graduate School
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I
Graduate Schools
Language: German
Originates at UBT: Yes
URN: urn:nbn:de:bvb:703-epub-3342-6
Date Deposited: 30 Aug 2018 08:15
Last Modified: 30 Aug 2018 08:15
URI: https://epub.uni-bayreuth.de/id/eprint/3342

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