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Synthesis of the Fijiolides Dihydropentalene Core and Amino Acid
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 r...
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| Format: | Dissertation |
| Sprache: | Englisch |
| Veröffentlicht: |
Philipps-Universität Marburg
2018
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| Online Zugang: | PDF-Volltext |
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| Zusammenfassung: | 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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| Umfang: | 188 Seiten |
| DOI: | 10.17192/z2018.0212 |