Autor(en): | Stiasni, Nikola |
Titel: | Synthetic studies toward the total synthesis of berkelic acid and lytophilippine A |
Sprache (ISO): | en |
Zusammenfassung: | C16-C20 part of natural product berkelic acid containing two adjacent stereogenic centers has been synthesized employing catalytic asymmetric Gosteli-Claisen rearrangement of 2 alkoxycarbonyl-substituted allyl vinyl ether as a key step. Synthetic sequence leading to the both fragments included 11 linear steps and afforded final products in good to excellent diastereoselectivity and good enantioselectivity. Model study exploring Oxa-Pictet-Spengler condensation as a key coupling step toward the tetracyclic core of berkelic acid has been successfully accomplished. C20-C27 fragment of lytophilippine A has been synthesized in a sequence of 13 linear steps, and in total yield of 8.4%. The synthesis commenced with readily available natural (+) L ascorbic acid and features Evans asymmetric alkylation and asymmetric aldol condensation with norephedrine-derived auxiliary as key steps to install the required C21-C23 anti, syn stereotriad. |
Schlagwörter: | Berkelic acid Lytophilippine A |
URI: | http://hdl.handle.net/2003/27643 http://dx.doi.org/10.17877/DE290R-8830 |
Erscheinungsdatum: | 2011-03-08 |
Enthalten in den Sammlungen: | Organische Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
---|---|---|---|---|
Dissertation.pdf | DNB | 1.04 MB | Adobe PDF | Öffnen/Anzeigen |
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