Rhodium-Catalyzed Imine-Directed C-H Bond Activation. Biomimetic Synthesis of Sesquiterpenoids

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1 Diss. ETH No Rhodium-Catalyzed Imine-Directed C-H Bond Activation And Biomimetic Synthesis of Sesquiterpenoids A dissertation submitted to ETH ZURICH For the degree of Doctor of Sciences Presented by Duc Tran Ngoc Diplôme d Ingénieur de l ENS de Chimie de Montpellier, France Born November 4th, 1985 Citizen of Vietnam Accepted on the recommendation of Prof. Dr. Erick M. Carreira, examiner Prof. Dr. Jeffrey W. Bode, co-examiner Prof. Dr. Nicolai Cramer, co-examiner Zürich 2014

2 VII Abstract The first part of my thesis describes the investigation of carbon-hydrogen bond activation processes. These newly developed transformations provide a facile and expedient access to a variety of complex structures. In our study, we developed new reaction conditions where the directing group, free ketimine, participated in the course of the reaction via a cascade pathway. The reaction is initiated by directed C-H activation catalyzed by rhodium (I) to form rhodacycle I. This common intermediate can perform a migratory insertion with different unsaturated bonds, followed by readdition to the ketimine to afford heavily substituted indanylamine derivatives. Terminal allenes were utilized as coupling partners to produce methylene-indenylamines II in high yields and diastereoselectivities. Subsequent lactamization could occur in a tandem fashion as an alternative downstream reaction (compound III). Dynamic kinetic asymmetric transformation was exploited with racemic internal allenes to achieve enantioenriched IV. Further substitution paterns on allenes were possible, yielding highly substituted indenylamines with two vicinal quaternary centers and a trisubstituted olefin such as V. Alkynes were efficient coupling partners yielding inden-1-amines VI in high enantioselectivities. The thesis will discuss in detail our studies of this formal [3+2] process in order to attain high stereoselectivities.

3 VIII The second part of the thesis is devoted to the total synthesis of terpenoids derived from bicyclogermacrene and caryophyllene. Terpenes are very abundant in all organisms and are the precursors of several biological active molecules. According to the proposed biosynthesis, plants rapidly creates these complex molecules from pre-organized terpenes. Our goal was to elaborate a synthetic route towards this family as well as to explore their reactivity in biomimetic transformations. This approach will not only provide a rapid access to the corresponding terpenoids but also confirm their proposed biosynthesis. Our initial idea was successfully applied to the first total synthesis of psiguadial B. This complex structure could be constructed in a single step starting from widely available sesquiterpene, caryophyllene, with careful optimization of the reaction conditions. Bicyclogermacrene, a bicyclic sesquiterpene, was prepared in 7 steps from 2-carene in 24 % yield. The key step of this synthesis was a stereoselective SmI 2 -mediated pinacol coupling which allowed construction of the highly strained ten-membered ring. In turn, bicyclogermacrene demonstrated versatile reactivity to be transformed into several terpenoids (spathulenol, ledene, viridiflorol and palustrol) and meroterpenoids (psiguadial A, C and D) with high selectivity.

4 IX

5 X Zusammenfassung Der erste Teil meiner Doktorarbeit beinhaltet die Untersuchung verschiedener Kohlenstoff-Wasserstoff-Bindungs aktivierungen. Diese neu entwickelten Reaktionen ermöglichen neuartige, vorteilhafte Zugänge zu komplexen Strukturen. In unseren Untersuchungen entwickelten wir freie Ketimine als neue dirigierende Gruppe welche im Reaktionsverlauf kaskadenartig reagieren. Die Reaktion wird durch eine Rhodium(I) katalysierte, dirigierte C-H-Aktivierung eingeleitet, wobei sich Rhodacyclus I bildet. Dieses gemeinsame Intermediat kann durch migratorische Insertion an diverse Mehrfachbindungen, gefolgt von der Addition des Ketimins, hochsubstituierte Indanylaminderivate bilden. Endständige Allene wurden als Kupplungspartner verwendet und ergaben Methylen-Indenylamine II in hohen Ausbeuten und Diastereoselektivitäten. Anschließende Lactamisierung ermöglicht den raschen Anstieg an molekularer Komplexität (Verbindung III). Dynamisch-kinetische asymmetrische Transformation wurde ausgenutzt um aus racemischen 1,2 disubstituierten Allenen enantiomerenangereicherte Verbindungen des Typs IV zu erhalten. Höhere Substitutionsmuster am Allen waren ebensfalls möglich und führten zu hochsubstituierten Indenylaminen mit zwei benachbarten quaternären Zentren und einem trisubstituierten Olefin, wie in Verbindung V gezeigt. Mit Alkinen als Reaktionspartner wurden Indenyl- 1-amine VI in hohen Enantioselektivitäten erhalten. Diese Arbeit wird unsere Untersuchungen zu diesen formalen [3+2] Additionen im Detail diskutieren.

6 XI Der Zweite Teil der Arbeit befasst sich mit Totalsynthesen verschiedener von Bicyclogermacren und β-caryophyllen abgeleiteter Terpenoide. Terpene sind in allen Organismen ubiquitär und dienen als Vorstufen für eine Fülle an biologisch aktiven Verbindungen. Laut der vorgeschlagenen Biosynthesen werden jene komplexen Moleküle rasch aus vororganisierten Terpenen gebildet. Unser Ziel war es diese Moleküle durch unterschiedliche Kaskadenreaktionen auf biomimetischen Weg zu synthetisieren. Ein solcher Ansatz würde nicht nur einen schnellen Zugang zu diesen Strukturen gewähren, sondern auch die vorgeschlagenen Biosynthesewege stützen. Unser Konzept fand erfolgreiche Anwendung bei der Erstsynthese von Psiguadial B. Ausgehend vom kommerziell erhältlichen β-caryophyllen, konnte diese komplexe Struktur mittels sorgfältiger Optimierung der Reaktionsbedingungen in einer einzigen Stufe erhalten werden.

7 XII Bicyclogermacren, ein bicyclisches Sesquiterpene, wurde in 7 Schritten mit 24 % Ausbeute von 2-Caren erhalten. Der Schlüsselschritt der Synthese war eine stereoselektive SmI 2 vermittelte Pinakol-Kupplung, welche den Aufbau des hochgespannten Ringsystems ermöglicht. Bicyclogermacrene wiederum erwies sich als vielseitiger Ausgangspunkt zur hochselektiven Synthese verschiedener Terpenoide (Spathulenol, Leden, Viridiflorol and Palustrol) und mero-terpenoide (Psiguadial A, C and D).

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