Dokument
| Titel: | Synthesis of the Fijiolides Dihydropentalene Core and Amino Acid |
| Autor: | Kurzawa, Timon |
| Weitere Beteiligte: | Koert, Ulrich (Prof. Dr.) |
| Veröffentlicht: | 2018 |
| URI: | https://archiv.ub.uni-marburg.de/diss/z2018/0212 |
| DOI: | https://doi.org/10.17192/z2018.0212 |
| URN: | urn:nbn:de:hebis:04-z2018-02128 |
| DDC: | 540 Chemie |
| Titel (trans.): | Synthese des Dihydropentalenkerns und der Aminosäureeinheit von Fijiolid A |
| Publikationsdatum: | 2019-01-15 |
| Lizenz: | https://creativecommons.org/licenses/by-nc-sa/4.0 |
| Schlagwörter: |
|---|
| 1,4-Addition, Organische Synthese, 1,4-Addition, CH-Aminierung, Benzodihydropentalen, CH-Amination, Fijiolide A, Präparative organische Chemie, Organische Chemie, Organic Synthesis, benzodihydropentalene, Fijiolid A |
Summary:
In this thesis, a stereoselective access to the benzodihydropentalene core structure 79 and the amino acid fragment 81 of the fijiolides was developed. For benzodihydropentalene 79 the synthetic strategy relied on introduction of a styryl moiety onto indenone 84 allowing construction of ring C via ring closing metathesis. Essential for this strategy was the early introduction of the alcohol at C9, that enabled the cis-arrangement of the previously installed allyl and the styryl moiety. Although the fijiolides` core does not contain a stereocenter at C1, enantioselective introduction of the styryl residue in this position allowed to build up the cyclopentadienol in a stereocontrolled fashion with a high degree of substrate control.
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