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Synthesis 2010(11): 1787-1792  
DOI: 10.1055/s-0029-1218764
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Spherical Polyols from Itaconic Acid

Céline Reynauda, Henri Doucet*b, Maurice Santelli*a
a Laboratoire Chimie Provence, associé au CNRS, UMR 6264, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
Fax: +33(4)91289112; e-Mail: m.santelli@univ-cezanne.fr;
b Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes ‘Catalyse et Organometalliques’, Campus de Beaulieu, 35042 Rennes, France
Fax: +33(2)23236939; e-Mail: henri.doucet@univ-rennes1.fr;
Further Information

Publication History

Received 22 January 2010
Publication Date:
29 April 2010 (online)

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Abstract

The Diels-Alder reaction of some bromo derivatives of the itaconic acid with cyclopenta-1,3-diene gave a simple access to precursors of spherical polyols of synthetic interest.

Key words

bicyclic compounds - Diels-Alder reaction - ozonolysis - stereoselective synthesis - protecting groups

    References

  • 1a Fringuelli F. Taticchi A. Dienes in the Diels-Alder Reaction   Wiley; New York: 1990. 
    Google Scholar
  • 1b Winkley JD. Chem. Rev.  1996,  96:  167 
    Google Scholar
  • 2a Laurenti D. Feuerstein M. Pèpe G. Doucet H. Santelli M. J. Org. Chem.  2001,  66:  1633 
    Google Scholar
  • 2b Reynaud C. Fall Y. Feuerstein M. Doucet H. Santelli M. Tetrahedron  2009,  65:  7440 
    Google Scholar
  • 2c Doucet H. Santelli M. Synlett  2006,  2001 
    Google Scholar
  • 2d Lemhadri M. Battace A. Berthiol F. Zair T. Doucet H. Santelli M. Synthesis  2008,  1142 
    Google Scholar
  • 2e Lemhadri M. Fall Y. Doucet H. Santelli M. Synthesis  2009,  1021 
    Google Scholar
  • 3a Garbers CF. Labuschagne AJH. Meyer CJ. Schneider DF. J. Chem. Soc., Perkin Trans. 1  1973,  2016 
    Google Scholar
  • 3b See also: Beltaïef I. Besbes R. Amri H. Villiéras J. Tetrahedron Lett.  1997,  38:  813 
    Google Scholar
  • 3c See also: Pelletier SW. Djamarti Z. Lajšić SD. Mićović IV. Yang DTC. Tetrahedron  1975,  31:  1659 
    Google Scholar
  • 4 For an efficient synthesis (90%) of 2 by the ring-closing metathesis reaction, see: Selvakumar N. Kumar PK. Reddy KCS. Chary BC. Tetrahedron Lett.  2007,  48:  2021 
    CrossrefGoogle Scholar
  • 5 Hoye TR. Caruso AJ. Magee AS. J. Org. Chem.  1982,  47:  4152 
    CrossrefGoogle Scholar
  • 6 For a selective protection of diol 5, see: Lee J. Barchi JJ. Marquez VE. Chem. Lett.  1995,  299 
    CrossrefGoogle Scholar
  • 7 Veysoglu T. Mitscher LA. Swayze JK. Synthesis  1980,  807 
    Article in Thieme ConnectGoogle Scholar
  • 8 Ozonolysis of a polyfunctionalized norbornene derivative can lead to an ‘oxa bowl’ having a crownlike shape, see: Mehta G. Vidya R. J. Org. Chem.  2001,  66:  6905 
    CrossrefGoogle Scholar
  • 9a Tomalia DA. Naylor AM. Goddard WA. Angew. Chem., Int. Ed. Engl.  1990,  29:  138 
    Google Scholar
  • 9b Rogunova M. Lynch T.-YS. Pretzer W. Kulzick M. Hiltner A. Baer E. J. Appl. Polym. Sci.  2000,  77:  1207 
    Google Scholar
  • 9c Fréchet J. Science  1994,  263:  1710 
    Google Scholar
  • 10 Lee TV. Toczek J. Tetrahedron Lett.  1985,  26:  473 
    CrossrefGoogle Scholar
  • 11a Greenlee WJ. Woodward RB. Tetrahedron  1980,  36:  3367 
    Google Scholar
  • 11b Buttler T. Fleming I. Gonsior S. Kim B.-H. Sung A.-Y. Woo H.-G. Org. Biomol. Chem.  2005,  3:  1557 
    Google Scholar
  • 12a Heissler D. Jung F. Vevert JP. Riehl JJ. Tetrahedron Lett.  1976,  4879 
    Google Scholar
  • 12b Ranganathan S. Ranganathan D. Mehrotra AK. Tetrahedron  1977,  33:  807 
    Google Scholar
  • 13 Komarov IV. Monsees A. Kadyrov R. Fisher C. Schmidt U. Börner A. Tetrahedron: Asymmetry  2002,  13:  1615 
    CrossrefGoogle Scholar
  • 14 Grob CA. Angew. Chem., Int. Ed. Engl.  1969,  8:  535 
    CrossrefGoogle Scholar
  • 15a Bertrand M. Monti H. Huong KC. Tetrahedron Lett.  1979,  20:  15 
    Google Scholar
  • 15b Ismail ZM. Hoffmann HMR. J. Org. Chem.  1981,  46:  3549 
    Google Scholar
  • 15c Hoffmann HMR. Ismail ZM. Weber AJ. Tetrahedron Lett.  1981,  22:  1953 
    Google Scholar
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X-ray crystallography: CCDC-767345 (for endo-4) and CCDC-767346 (for 10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or e-mail: deposit@ccdc.cam.ac.uk].