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        Synthesis  2010(22): 3883-3890  
DOI: 10.1055/s-0030-1258263
   DOI: 10.1055/s-0030-1258263
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkSynthesis of Enantiomerically Pure 2,5-Disubstituted 3-Oxygenated Tetrahydrofurans
Weitere Informationen
            
               
                  
                        
                              Received
                              26 July 2010 
                      
Publikationsdatum:
22. September 2010 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
22. September 2010 (online)

Abstract
The synthesis of enantiomerically pure 2,5-disubstituted 3-oxygenated tetrahydrofurans has been achieved from cheap and commercially available l-malic acid. This method was used to prepare an advanced intermediate toward CMI-977, a promising candidate for the treatment of chronic asthma.
Key words
furan - tetrahydrofuran - singlet oxygen - butenolide - oxacycles - natural products
- 1 
             
            Capon RJ.Barrow RA.Rochfort S.Jobling M.Skene C.Lacey E.Gill JH.Friedl T.Wadsworth D. Tetrahedron 1998, 54: 2227
- 2 
             
            Warren RG.Wells RJ.Blount JF. Aust. J. Chem. 1980, 33: 891
- 3a 
             
            Gadikota RR.Callam CS.Lowary TL. J. Org. Chem. 2001, 66: 9046Reference Ris Wihthout Link
- 3b 
             
            Nesbitt CL.McErlean CSP. Tetrahedron Lett. 2009, 50: 6318 ; and references cited thereinReference Ris Wihthout Link
- 4 
             
            Suzuki T.Koizumi K.Suzuki M.Kurosawa E. Chem. Lett. 1983, 1643
- 5 
             
            Suzuki T.Koizumi K.Suzuki M.Kurosawa E. Chem. Lett. 1983, 1639
- 6a 
             
            Brown MJ.Harrison T.Overman LE. J. Am. Chem. Soc. 1991, 113: 5378Reference Ris Wihthout Link
- 6b 
             
            Grese TA.Hutchinson KD.Overman LE. J. Org. Chem. 1993, 58: 2468Reference Ris Wihthout Link
- 6c 
             
            Osumi K.Sugimura H. Tetrahedron Lett. 1995, 36: 5789Reference Ris Wihthout Link
- 6d 
             
            Lee E.Yoo S.-K.Cho Y.-S.Cheon H.-S.Chong YH. Tetrahedron Lett. 1997, 38: 7757Reference Ris Wihthout Link
- 6e 
             
            Boukouvalas J.Fortier G.Radu I.-I. J. Org. Chem. 1998, 63: 916Reference Ris Wihthout Link
- 6f 
             
            Evans PA.Murthy VS.Roseman JD.Rheingold AL. Angew. Chem. Int. Ed. 1999, 38: 3175Reference Ris Wihthout Link
- 6g 
             
            Braddock DC.Bhuva R.Millan DS.Pérez-Fuentes Y.Roberts CA.Sheppard RN.Solanki S.Stokes ES. E.White AJ. P. Org. Lett. 2007, 9: 445Reference Ris Wihthout Link
- 7a 
             
            Eugster CH. Helv. Chim. Acta 1956, 39: 1002Reference Ris Wihthout Link
- 7b 
             
            Kögl F.Salemink CA.Schouten H.Jellinek F. Recl. Trav. Chim. Pays Bas 1957, 76: 109Reference Ris Wihthout Link
- 7c 
             
            Eugster CH. Naturwissenschaften 1968, 55: 305Reference Ris Wihthout Link
- 7d 
             
            Bollinger H.Eugster CH. Helv. Chim. Acta 1971, 54: 2704Reference Ris Wihthout Link
- 8 
             
            Nitta K.Stadelmann RJ.Eugster CH. Helv. Chim. Acta 1977, 60: 1747
- 9a 
             
            Eugster CH.Müller G. Helv. Chim. Acta 1959, 42: 1189Reference Ris Wihthout Link
- 9b 
             
            List HP.Müller H. Arch. Pharm. 1959, 292: 777Reference Ris Wihthout Link
- 9c 
             
            Catalformo P.Eugster CH. Helv. Chim. Acta 1970, 53: 848Reference Ris Wihthout Link
- 9d 
             
            Bollinger H.Eugster CH. Helv. Chim. Acta 1971, 54: 1332Reference Ris Wihthout Link
- 10a 
             
            Popsavin V.Popsavin M.Radic L.Beric O.Cirin-Novta V. Tetrahedron Lett. 1999, 40: 9305Reference Ris Wihthout Link
- 10b 
             
            Kang KH.Cha MY.Pae AN.Choi KL.Cho YS.Koh HY.Chung BY. Tetrahedron Lett. 2000, 41: 8137Reference Ris Wihthout Link
- 10c 
             
            Hartung J.Kneuer R. Tetrahedron: Asymmetry 2003, 14: 3019Reference Ris Wihthout Link
- 11a 
             
            Gurjar MK.Murugaiah AMS.Radhakrishna P.Ramana CV.Chorghade MS. Tetrahedron: Asymmetry 2003, 14: 1363Reference Ris Wihthout Link
- 11b 
             
            Sharma GVM.Punna S.Rajendra Prasad T.Krishna PR.Chorgade MS.Ley SV. Tetrahedron: Asymmetry 2005, 16: 1113Reference Ris Wihthout Link
- 11c 
             
            Sharma GVM.Punna S.Krishna PR.Chorghade MS.Ley SV. Tetrahedron: Asymmetry 2005, 16: 1125Reference Ris Wihthout Link
- 12a 
             
            Fall Y.Vidal B.Alonso D.Gómez G. Tetrahedron Lett. 2003, 44: 4467Reference Ris Wihthout Link
- 12b 
             
            Pérez M.Canoa P.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2004, 45: 5207Reference Ris Wihthout Link
- 12c 
             
            Alonso D.Pérez M.Gómez G.Covelo B.Fall Y. Tetrahedron 2005, 61: 2021Reference Ris Wihthout Link
- 12d 
             
            Teijeira M.Suárez PL.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2005, 46: 5889Reference Ris Wihthout Link
- 12e 
             
            García I.Gómez G.Teijeira M.Terán C.Fall Y. Tetrahedron Lett. 2006, 47: 1333Reference Ris Wihthout Link
- 12f 
             
            Canoa P.Pérez M.Covelo B.Gómez G.Fall Y. Tetrahedron Lett. 2007, 48: 3441Reference Ris Wihthout Link
- 13 
             
            Hanessian S.Tehim A.Chen P. J. Org. Chem. 1993, 58: 7768
- 14 
             
            Hanessian S.Ugolini A.Dubé D.Glamyan A. Can. J. Chem. 1984, 62: 2146
- 15 
             
            Kumara Swamy KC.Bhuvan Kumar NN.Balaraman E.Pavan Kumar KVP. Chem. Rev. 2009, 109: 2551
- 16 
             
            Canoa P.Vega N.Pérez M.Gómez G. Tetrahedron Lett. 2008, 49: 1149
 
    