0~te (>/w*r SYNTHESIS OF NUCLEOSIDE ANALOGS. Dipl. Chem. FU Berlin. Accepted on the recommendation of ZÜRICH. Diss. ETH Nr. 8841
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1 Diss. ETH Nr SYNTHESS OF NUCLEOSDE ANALOGS A dissertation submitted to the SWSS FEDERAL NSTTUTE OF TECHNOLOGY ZÜRCH for the degree of Doctor of Natural Sciences Presented by KLAUS CHRSTAN SCHNEDER Dipl. Chem. FU Berlin MA Harvard University born October 16,1960 Citizen of the USA Accepted on the recommendation of Prof. Dr. Steven A. Benner, examiner Prof. Dr. Dieter Seebach, co-examiner 0~te (>/w*r ADAG Administration & Druck AG Zürich 1989
2 <C02H ABSTRACT Oligonucleotide analogs containing dimethylene sulfone bridges replacing the natural phosphodiester linkage are of potential interest as research tools for selective inhibition of gene expression and as pharmaceutical agents. Described here are two synthetic routes to the building blocks 120 for such DNA isosters. One route Starts with a Diels-Alder reaction between butadiene and acetoxy-ethylacrylate to yield 13, and proceeds via PLE-catalyzed enantioselective hydrolysis of the racemic mixture of ester (±)15 to furnish enantiomerically pure (-)17. Ozonolysis of intermediate 23 leads after selective acetalization and reduction to 32. Cyclisation of this molecule furnishes 34 into which the nucleoside bases are incorporated. After seperation of the anomeric mixtures obtained, functional group manipulation then leads to the target molecules 120. /\.*,C02fct,,<C02Et /v.,<uu2h o o <-)17 'OAc ^^'''OBz \-^"'OBz a^coütt <±)1S BzO 120: B N -benzoyladenine (47), N -isobutyrylguanine (50), N -benzoylcytosine (52), uracil (54) n the second route 66, obtained from diacetone glucose, is transformed via a five step sequence to 75. Cyclisation of 75 leads to 77 which is derivatized to 80 preparing the molecule for stereoselective base incorporation and subsequent photochemical deoxygenation to give nucleoside analog 81. ntroduction of the thioacetate moiety then furnishes target molecule. 54. X o- o-
3 ntermediate 83 also serves, via thioacetate 85, as a precursor to the ribo-forms of the nucleoside analogs 120. HO OAc AcO ' OAc : B = uracil, 87: B = N -benzoylcytosine, 88: B = N -benzoyladenine n preliminary studies towards acyclic nucleoside analogs, racemic mixtures of the monomers 105, 106 and 108 were synthesised starting from dimethylhydroxyglutarate. MeOCON^JSv^C02Me N 105:B = A 106:B = C Further, monomers were prepared for coupling by blocking the sulfur as the methyl sulfone and activating the oxygen as its mesylate (112, 117). Coupling was finally achieved by condensation of 112 and 117 with mercapto alcohols 109 and 114 to give dimers 113 and 118, respectively. Me-SO, U- vj P ll2' '" > 109, , 109, 112, 113: B = Uracil 47, 114, 117, 118: B = N6-Benzoyladenine
4 Zusammenfassung Oligonu-kleotid-Analoga, die Dimethylensulfon-Brücken anstelle der natürlichen Phosphordiester-Brücken enthalten, sollten die Expression von Genen spezifisch inhibieren können. Solche Verbindungen sind daher als Forschungswerkzeuge und Pharmazeutica von nteresse. Hier werden zwei Synthesewege zu den Bausteinen 120 für solche, zu DNA isosteren, Oligonucleotid-Analoga beschrieben. Ein Syntheseweg begann mit einer Diels-Alder Reaktion von Butadien mit Acetoxyacrylsäureethylester zu 13, gefolgt von einer PLE-katalysierten enantioselektiven Hydrolyse des racemischen Esters (±)15 zur enantiomerenreinen Säure (-)17. Ozonolyse des Zwischenproduktes 23 führte, nach selektiver Acetalisierung und anschließender Reduktion, zu 32. Zyklisierung dieses Moleküls ergab 34, in das die Nukleosid- Basen eingeführt wurden. Auftrennung des erhaltenen Anomerengemisches und Einführung der Thioestergruppe führte zu den Zielverbindungen tx O vicojet tj. vcojh OAc ^^>OAc ^/"'OBz \^"'OBz 13 ( + )15 (-J17 120: B = N -benzoyladenin (47), N -sobutyrylguanin (50), N -benzoylcytosln (52), uracil (54) n der zweiten Route wurde 66, das aus Diacetonglucose hergestellt wurde, über eine fünfstufige Reaktionssequenz in 75 überführt. Durch Zyklisierung von 75 zu 77 und anschließende Veresterung von 77 zu 80 wurde das Molekül für die stereoselektive Einführung der Basen und die darauf-
5 folgende photochemische Deoxygenierung zu 81 vorbereitet. Bildung der Thioesterfunktion führte dann zu 54. Analoga HO Die, analog zu 75 hergestellte Verbindung 83 diente auch, über den Thioester 85, als Edukt zur Synthese der Ribonukleosid- ^'\ _^/ s0ac V^B ft- > \ Y-A W w 1 AcOl\ AcO- J OAc AcO 1 OAc : B = uracil, 87: B = N -benzoylcytosin, 88: B = N -benzoyladenin n vorläufigen Studien zur Synthese von azyklischen Nukleosid- Analoga wurden, ausgehend von Hydroxyglutarsäuredimethylester, die Bausteine 105, 106 und 108, jeweils in racemischer Form, synthetisiert. MaOCO^Js^COzMe Vj lo L-opv :B = A 106:B = C Weiterhin wurden Bausteine durch Blockierung des Schwefels in Form des Methylsulfons und Aktivierung der Hydroxylgruppe als Mesylat zur Kopplung vorbereitet (112, 117). 112 und 117 wurden schließlich mit den Mercaptoalkoholen 109 bzw. 114 zu den Dimeren 113 bzw. 118 kondensiert. n/ vj r "7 112, 117 L_ OMs 54, 109, 112, 113: B = Uracil 47, 114, 117, 118: B - N6-Benzoyladenin
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