Towards a Structural Revision of Mytilipin B
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1 Research Collection Doctoral Thesis Towards a Structural Revision of Mytilipin B Author(s): Jacobsen, Mathias Juul Publication Date: 2016 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 DISS. ETH NO Towards a Structural Revision of Mytilipin B A thesis submitted to attain the degree of DOCTOR OF SCIENCES of ETH ZURICH (Dr. sc. ETH Zurich) presented by MATHIAS JUUL JACOBSEN MSc, Aarhus University born on citizen of Denmark accepted on the recommendation of Prof. Dr. Erick M. Carreira, examiner Prof. Dr. Karl-Heinz Altmann, co-examiner 2016
3 vii Abstract Chlorosulfolipids, an unusual class of polychlorinated natural products, were first detected in the late 1960 s by Elovson and Vagelos in extracts from Ochromonas danica. In the early 2000 s, Ciminiello and Fattorusso isolated mytilipins A, B, and C from the digestive glands of mussels, Mytilus galloprovincialis, collected along the Emilia Romagna coastline of Italy (Chart 1). These compounds were suspected to be causative agents for diarrhetic shellfish poisoning. The structures of the mytilipins were assigned based on extensive analyses of NMR spectral data and Mosher ester analysis. The relative configurations were assigned based on J-Based Conformational Analysis (JBCA). Chart 1 Structure of mytilipin A and proposed structures of mytilipins B and C. In 2009, Carreira et al. disclosed a synthesis of mytilipin A, constituting the first total synthesis of a chlorosulfolipid, and in 2011 they further documented the total synthesis of nominal mytilipin B, the most complex chlorosulfolipid isolated to date. A comparison of NMR spectral data for II showed severe mismatches between the isolation report and the data obtained for the synthetic material. Hence, a misassignment of the structure by the isolation group was concluded. This thesis describes our work on a structural revision of mytilipin B and the synthetic studies towards a confirmation of the structure by total synthesis. By careful reinvestigation of the isolation data, we observed a key discrepancy in interpretation of a ROESY spectrum which leads to a different conclusion in a JBCA (Chart 2). The isolation group reported the presence of a ROE crosspeak between H12 and H15, however, this signal is absent in the reported data. Accordingly, the C13/C14 relative configuration should be anti as opposed to the reported syn-relationship. Ultimately, this leads to a revision of the configuration of five stereogenic centers in the area C14 C19 (Chart 2). In addition, it is noted that a correction of the C23 configuration might be necessary due to incorrect use of a Mosher ester analysis, however, the (S) and (R) configuration at C23 is equally plausible from our analysis.
4 viii Chart 2 Structural revision of mytilipin B based on an absent ROE crosspeak. In synthetic studies towards revised mytilipin B (IV), synthesis of both fragments VII and VIII followed by unification in a Julia Kocienski olefination reaction has been achieved (Scheme 1). Fragment VIII was prepared on the basis of known protocols, and the present work describes additional observations, improvements, and attempts at alternative strategies. Fragment VII was prepared in 17 steps from L-malic acid via primary alcohol V. Key transformations to afford VII include trans-specific dichlorinations, a Sharpless epoxidation, and a highly cis-selective Wittig olefination reaction. From coupling product IX, epoxide opening, dichlorination, and deprotection/dehydration allowed for the successful completion of the entire hydrocarbon backbone structure X as the most advanced intermediate obtained in this work towards revised mytilipin B (IV). Scheme 1 Synthetic studies towards revised mytilipin B.
5 ix Zusammenfassung Chlorosulfolipide, eine ungewöhnliche Klasse polychlorierter Naturstoffe, wurden erstmals in den späten 1960er Jahren von Elovson und Vagelos aus Extrakten von Ochromonas danica isoliert. Anfang des 21. Jahrhunderts isolierten Ciminiello und Fattorusso die Naturstoffe Mytilipin A, B und C aus den Verdauungsdrüsen von Muscheln der Gattung Mytilus galloprovincialis, die entlang der Küste von Emilia Romagna in Italien gesammelt wurden (Abbildung 1). Diese Verbindungen wurden verdächtigt Erreger diarrhöischer Schalentiervergiftung zu sein. Die Strukturen der Mytilipine wurden auf Basis von umfangreichen NMR-Daten und Mosher-Ester Analysen zugeordnet. Die relativen Konfigurationen wurden anhand von J-basierter Konformationsanalyse (JBCA) zugeordnet. Abbildung 1 Struktur von Mytilipin A und vorgeschlagene Strukturen von Mytilipin B und C. Im Jahr 2009 veröffentlichten Carreira et al. die erste Totalsynthese eines Chlorosulfolipids, Mytilipin A. Eine nachfolgende Arbeit im Jahr 2011 beschrieb die Totalsynthese von nominellem Mytilipin B, des bis dato komplexesten Chlorosulfolipids. Die NMR Daten des Naturstoffs wichen allerdings gravierend von denen des synthetischen Materials (II) ab. Dieses Ergebnis legte eine Fehlzuordnung der Struktur durch die Isolationsgruppe nahe. Diese Dissertation beschreibt unsere Arbeit an einer strukturellen Revision von Mytilipin B sowie synthetische Studien auf dem Weg zu einer experimentellen Bestätigung der Struktur. Bei der sorgfältigen Überprüfung der Isolationsdaten bemerkten wir eine wesentliche Diskrepanz bei der Interpretation eines ROESY-Spektrums, die in der JBCA-Analyse zu einem anderen Ergebnis führt (Abbildung 2). Die Isolationsgruppe beschrieb ein ROE-Kreuzsignal zwischen H12 und H15, welches allerdings in den Originaldaten nicht zu finden ist. Dementsprechend sollte eine relative anti-konfiguration an C13/C14 bestehen, statt der beschriebenen syn-konfiguration. Letztendlich führt dies zu einer Revision der Konfiguration von fünf stereogenen Zentren zwischen C14 und C19 (Abbildung 2). Darüber hinaus ist es möglich, dass die Konfiguration von C23 aufgrund der falschen
6 x Anwendung einer Mosher-Ester Analyse korrigiert werden muss. Unserer Analyse nach sind beide Konfigurationen gleichermaßen plausibel. Abbildung 2 Strukturelle Revision von Mytilipin B aufgrund eines nicht vorhandenen ROE-Kreuzsignals. In synthetischen Studien zur revidierten Struktur von Mytilipin B (IV) wurden die beiden Fragmente VII und VIII erfolgreich dargestellt und mittels einer Julia-Kocienski Olefinierung gekoppelt (Schema 1). Fragment VIII wurde auf der Grundlage bekannter Protokolle hergestellt und die vorliegende Arbeit beschreibt zusätzliche Beobachtungen, Verbesserungen und Studien zu alternativen Strategien. Ausgehend von L-Äpfelsäure wurde Fragment VII über den primären Alkohol V in 17 Schritten hergestellt. Schlüsselschritte auf dem Weg zu VII beinhalteten transspezifische Dihalogenierungen, eine Sharpless-Epoxidierung sowie eine besonders cis-selektive Wittig Olefinierung. Von Kopplungsprodukt IX führten Epoxidöffnung, Dichlorierung sowie Entschützung/Dehydratisierung zur erfolgreichen Darstellung des gesamten Kohlenstoffgerüsts. Struktur X stellt das fortgeschrittenste Intermediat dieser Arbeit auf dem Weg zu strukturell revidiertem Mytilipin B (IV) dar. Schema 1 Synthetische Studien auf dem Weg zu revidiertem Mytilipin B.
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