Research Collection. Total synthesis of erythronolide A via nitrile oxide cycloadditions. Doctoral Thesis. ETH Library. Author(s): Muri, Dieter
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1 Research Collection Doctoral Thesis Total synthesis of erythronolide A via nitrile oxide cycloadditions Author(s): Muri, Dieter Publication Date: 2005 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 Total Synthesisof Erythronolide A via Nitrile Oxide Cycloadditions A dissertationsubmitted to the Swiss Federal Institute of Technology ETH Zürich For the degree of Doctor of Sciences Presentedby DieterMuri Dipl. Natw. ETH Born September25, 1973 Citizen of Rain and Oberkirch,LU Acceptedon the recommendationof Prof. Dr. ErickM. Carreira, examiner Prof. Dr. Donald Hilvert, co-examiner Zürich, 2005
3 Total Synthesis oferythronolide A via Nitrile Oxide Cycloadditions page v Abstract Erythromycin A (I), one of the best known macrolide antibiotics, was isolated in 1952 by McGuire and co-workers from Saccharopolyspora erythraea (Figure I). It is used in clinical medicine against Gram-positive bacteria. Furthermore it finds application in the treatmentof many pulmonary patients allergic against penicillins. O infectionsand as an alternativefor «, l,1, m*j N? This thesis " Y? 0 0-7^-^- Erythromycin (I) Figure I describes the development of a magnesium-mediated nitrile oxide cycloaddition and its application to the synthesis of erythronolide A (X), the aglycon of erythromycin A (I). A general protoeol for the magnesium-mediatednitrile oxide cycloaddition of alkyl nitrile oxides with allylic alcohols was developed. The procedure accesses isoxazolines in high regio- and diastereoselectivity and allows for the formation of all possible dipropionate analogues IV in oximes II and allylic alcohols III (EquationI). a single step from easily accessible chiral
4 page vi Abstract TBS? Ii + R^y rrvzn m'0h -. a)rbuoci,-78 C TBSO L. N- A ^k. H b) EtMgBr, 2-Pr CH2CI2 R H II III 0 C-RT IV R = H, n\ The total synthesis of erythronolide A (X) relies on the application of this cycloaddition reaction to assemble the key dipropionate fragment VII (Scheme I). Oxime VIII was accessed in nine steps from fragment VII, including a chelationcontrolled Grignard reaction. second nitrile oxide cycloaddition with allylic The highly substituted oxime VIII participated in a alcohol VI. Conversion of the cycloadditionproduct to the seco-acid IX proceeded in six steps and included a Z- selective Wittig reaction, followed by a Sharpless asymmetriedihydroxylation. TBSO N "Ma2+" I II I TBSO 0 0 N TBCn M- TBSO N 0 XD _ «A._ M-0H HO 1 " y L i! *. _-. fr I ^^v-'ivic Mo Mo ni- V X O O O V! RO "RJI^.2+" Mg R = TES VI X N O TBSO O O N O RO HO RO IX ii The macrolactonization proceeded Scheme I smoothly using Yamaguchi's conditions. Two deprotections and the reduetive opening of the isoxazoline completed the total synthesis of erythronolide A (X) (Scheme II).
5 Total Synthesisof ErythronolideA via Nitrile Oxide Cycloadditions page vu IX., HO OTES HO.,,<<.,,.«^,ok XI: R = TES,,J, ' Erythronolide A (X) Scheme II The synthesis of erythronolide A (X) was performed in 21 steps and 2.5% overall yield from oxime V. It highlights the potential of the magnesium-mediated nitrile oxide cycloaddition in the context of polyketidenarural-productsynthesis. In addition, a number of alternative synthetic efforts towards the synthesis of erythronolide A (X) are described. In this regard, the syntheses of the key macrolactones XII and XIII were successfully achieved (Figure II). However, the final steps describedin Scheme II proved superior in concluding the total synthesis of erythronolide A (X)..,,, OTES,i- '0 / ^/1^ p3 [, OTES ^ AJe, 'O "O XII XIII Figure II
6 Total SynthesisofErythronolideA via Nitrile Oxide Cycloadditions page ix Zusammenfassung Erythromycin A (I), eines der bekanntesten Macrolid-Antibiotika, wurde 1952 von McGuire und Mitarbeitern aus Saccharopolyspora erythraea isoliert (Figur I). Es wird in der klinischen dizin gegen Gram-positive Bakterien verwendet. Desweiteren kommt es gegen Lungeninfektionen und als Alternative für Patienten mit allergischenreaktionen gegenpenicillin zur Anwendung. O ^A. v, oht T,,U^0H^,- ^ 'O Erythromycin (I) O Figur I In dieser Arbeit wird die Entwicklung einer Magnesium-dirigierten Nitril-Oxid Cycloaddition und deren Anwendung in der Synthese von Erythronolid A (X), dem Aglycon von Erythromycin A (I), beschrieben. Eine allgemeingültige Reaktionsführung für die Magnesium-dirigierte Nitril- Oxid Cycloaddition von Alkylnitriloxiden mit allylischen Alkoholen wurde Regio- und Diastereoselektivität. Sie ermöglicht die Bildung aller möglicher Dipropionatanalogen IV mit einem einzigen Reaktionsschritt von einfach zugänglichen chiralen Oximen II und allylischenalkoholeniii (GleichungI). entwickelt. Die Reaktion erlaubt die Herstellung von Isoxazolinenin sehr guter
7 page x Zusammenfassung TBSO N trco m'0h ii + R^^ a) rbuoci,-78 C H b) EtMgBr, 2-Pr TBSO N 0 iii T T X, CH2CI2 R H II III 0 C-RT IV R = H, m Diese Cycloaddition wird verwendet zur Herstellung des Schlüssel- Dipropionatfragmentes VII bei der Totalsynthese von Erythronolide A (X) (Schema I). Ausgehendvon VII wurde Oxim VIII in 9 Schritten synthetisiert, wobei eine chelat-kontrollierte Grignard-Reaktion durchgeführt wurde. Mit dem hochsubstituierten Oxim VIII und dem allylischen Alkohol VI wurde eine weitere Cycloaddition durchgeführt. Die Seco-Säure wurde in sechs Schritten erhalten, welche eine Z-selektive Wittigreaktion, gefolgt von einer asymmetrischensharpless- Dihydroxylierung beinhalten. Tßc:n M- TBSO N O nxn nc>n TBSO N "Mg2+" I TBSO O O N HO -*- kl. I ^X^'V,t! Mn Kto nl 0H ^Y I RO wii V" V VI VI X O o o R = TES "Mg 2+<i N^ O TBSO 0 0 N 0 ^y VI RO HO RO IX Schema I Die Makrolaktonisierung wurde unter Yamaguchi-Bedingungen durchgeführt. Mit zwei Entschützungenund einer reduktivenöffnung des Isoxazolinringes wurde die Synthese von Erythronolid A (X) abgeschlossen(schema II).
8 Total Synthesisof Erythronolide A via Nitrile Oxide Cycloadditions page xi IX. HO OTES HO,n,,..< \ 0 'f O O^Y'"0^'" XI: R = TES '' Erythronolide A (X) Schema II Die Synthese von Erythronolid A (X) beinhaltet 21 Schritte, ausgehend von OximeV bis Endprodukt X und gelang in einer Gesamtausbeutevon 2.5%. Die kurze Synthese demonstriert die Nützlichkeit der Magnesium-dirigierten Nitriloxid Cycloaddition bei der Herstellung von komplexen Polykerid-Naturprodukten. Zusätzlich wurden noch alternativeversuchezur Synthesen von Erythronolid A (X) durchgeführt. Dabei wurden die wichtigen IntermediateXII und XIII hergestellt (Figur II). Der Syntheseweg, der in Schema II beschrieben wurde, hat sich als der bessere Weg zur vollständigensynthese von Erythronolid A (X) herausgestellt.. OTES,i-. OTES,n, "O 'O "O XII XIII Figur II
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MehrModelluntersuchungen zur Spülung und Gemischbildung in einem Verbrennungsmotor
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