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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
Further Information
Received
26 July 2010
Publication Date:
22 September 2010 (online)
Publication History
Publication Date:
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: 9046 - 3b
Nesbitt CL.McErlean CSP. Tetrahedron Lett. 2009, 50: 6318 ; and references cited therein - 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: 5378 - 6b
Grese TA.Hutchinson KD.Overman LE. J. Org. Chem. 1993, 58: 2468 - 6c
Osumi K.Sugimura H. Tetrahedron Lett. 1995, 36: 5789 - 6d
Lee E.Yoo S.-K.Cho Y.-S.Cheon H.-S.Chong YH. Tetrahedron Lett. 1997, 38: 7757 - 6e
Boukouvalas J.Fortier G.Radu I.-I. J. Org. Chem. 1998, 63: 916 - 6f
Evans PA.Murthy VS.Roseman JD.Rheingold AL. Angew. Chem. Int. Ed. 1999, 38: 3175 - 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: 445 - 7a
Eugster CH. Helv. Chim. Acta 1956, 39: 1002 - 7b
Kögl F.Salemink CA.Schouten H.Jellinek F. Recl. Trav. Chim. Pays Bas 1957, 76: 109 - 7c
Eugster CH. Naturwissenschaften 1968, 55: 305 - 7d
Bollinger H.Eugster CH. Helv. Chim. Acta 1971, 54: 2704 - 8
Nitta K.Stadelmann RJ.Eugster CH. Helv. Chim. Acta 1977, 60: 1747 - 9a
Eugster CH.Müller G. Helv. Chim. Acta 1959, 42: 1189 - 9b
List HP.Müller H. Arch. Pharm. 1959, 292: 777 - 9c
Catalformo P.Eugster CH. Helv. Chim. Acta 1970, 53: 848 - 9d
Bollinger H.Eugster CH. Helv. Chim. Acta 1971, 54: 1332 - 10a
Popsavin V.Popsavin M.Radic L.Beric O.Cirin-Novta V. Tetrahedron Lett. 1999, 40: 9305 - 10b
Kang KH.Cha MY.Pae AN.Choi KL.Cho YS.Koh HY.Chung BY. Tetrahedron Lett. 2000, 41: 8137 - 10c
Hartung J.Kneuer R. Tetrahedron: Asymmetry 2003, 14: 3019 - 11a
Gurjar MK.Murugaiah AMS.Radhakrishna P.Ramana CV.Chorghade MS. Tetrahedron: Asymmetry 2003, 14: 1363 - 11b
Sharma GVM.Punna S.Rajendra Prasad T.Krishna PR.Chorgade MS.Ley SV. Tetrahedron: Asymmetry 2005, 16: 1113 - 11c
Sharma GVM.Punna S.Krishna PR.Chorghade MS.Ley SV. Tetrahedron: Asymmetry 2005, 16: 1125 - 12a
Fall Y.Vidal B.Alonso D.Gómez G. Tetrahedron Lett. 2003, 44: 4467 - 12b
Pérez M.Canoa P.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2004, 45: 5207 - 12c
Alonso D.Pérez M.Gómez G.Covelo B.Fall Y. Tetrahedron 2005, 61: 2021 - 12d
Teijeira M.Suárez PL.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2005, 46: 5889 - 12e
García I.Gómez G.Teijeira M.Terán C.Fall Y. Tetrahedron Lett. 2006, 47: 1333 - 12f
Canoa P.Pérez M.Covelo B.Gómez G.Fall Y. Tetrahedron Lett. 2007, 48: 3441 - 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