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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Bibliographic Details
Main Author: Kurzawa, Timon
Contributors: Koert, Ulrich (Prof. Dr.) (Thesis advisor)
Format: Dissertation
Language:English
Published: Philipps-Universität Marburg 2018
Chemie
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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.
Physical Description:188 Pages
DOI:https://doi.org/10.17192/z2018.0212