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Synthesis 2012(1): 137-143  
DOI: 10.1055/s-0031-1289621
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Strategy for the Bis-Butenolide Synthesis via Ring-Closing Metathesis

Muriel Billamboza, Jean Christophe Legeaya, Frédéric Hapiotb, Eric Monflierb, Christophe Len*a
a Transformations Intégrées de la Matière Renouvelable, UTC- ESCOM, 1-Allée du réseau Jean-Marie Buckmaster, 60200 Compiègne, France
Fax: +33(3)44971591; e-Mail: Christophe.len@utc.fr;
b Université Lille Nord de France, UCCS, UMR 8181, UArtois, Faculté des Sciences Jean Perrin, Rue Jean Souvraz, SP 18, 62307 Lens cedex, France
Further Information

Publication History

Received 20 September 2011
Publication Date:
23 November 2011 (online)

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Abstract

A new synthesis to bis-butenolide derivatives from inexpensive divinylglycol is described, employing a sequential double acylation followed by a double ring-closing metathesis. The selectivity is affected by the choice of catalyst.

Key words

glycerol - pinacol - metathesis - ring closure - lactone

    References

  • 1 Li D.-H. Zhu T.-J. Liu HB. Fang Y.-C. Gu QQ. Zhu WM. Arch. Pharm. Res.  2006,  29:  624 
    Google Scholar
  • 2 Yadav P.-P. Arora A. Bid HK. Konwar RR. Kanojiya RR. Tetrahedron Lett.  2007,  48:  7194 
    Google Scholar
  • 3 Wright A.-D. Nys RD. Angerhofer C.-K. Pezzuto JM. Gurrath M. J. Nat. Prod.  2006,  69:  1180 
    Google Scholar
  • 4 Crimmins MT. Zhang Y. Diaz FA. Org. Lett.  2006,  11:  2369 
    Google Scholar
  • 5 Prasad KK. Gandi VR. Tetrahedron: Asymmetry  2010,  21:  275 
    Google Scholar
  • 6 Konno H. Makabe H. Hattori Y. Nosaka K. Akaji K. Tetrahedron  2010,  66:  7946 
    Google Scholar
  • 7 Choi H. Hwang H. Chin J. Kim E. Lee J. Nam SJ. Lee BC. Rho BJ. Kang H. J. Nat. Prod.  2011,  74:  90 
    Google Scholar
  • 8a Miao R. Gramani SG. Lear M.-J. Tetrahedron Lett.  2009,  50:  1731 
    Google Scholar
  • 8b Adrio J. Carretero JC. J. Am. Chem. Soc.  2007,  129:  778 
    Google Scholar
  • 8c Karioti A. Skaltsa H. Linden A. Perozzo R. Brun R. Tasdemir D. J. Org. Chem.  2007,  72:  8103 
    Google Scholar
  • 8d Martin SF. Barr KJ. J. Am. Chem. Soc.  1996,  118:  3299 
    Google Scholar
  • 8e Sheldrake HM. Jamieson C. Pascu SI. Burton JW. Org. Biomol. Chem.  2009,  7:  238 
    Google Scholar
  • 9a Fegyverneki D. Orha L. Láng G. Horváth IT. Tetrahedron  2010,  66:  1078 
    Google Scholar
  • 9b Bond JQ. Alonso DM. Wang D. West RM. Dumesic JA. Science  2010,  327:  1110 
    Google Scholar
  • 10a Bilenko V. Spannenberg A. Baumann W. Komarov I. Börner A. Tetrahedron: Asymmetry  2006,  17:  2082 
    Google Scholar
  • 10b Maier M.-E. Reuter S. Synlett  1995,  1029 
    Google Scholar
  • 10c Behr S. Hegemann K. Schimanski H. Fröhlich R. Haufe G. Eur. J. Org. Chem.  2004,  3884 
    Google Scholar
  • 10d Gourdel Y. Pellon P. Toupet L. Le Corre M. Tetrahedron Lett.  1994,  35:  1197 
    Google Scholar
  • 10e Schmidt B. Staude L. Kelling A. Schilde U. Eur. J. Org. Chem.  2011,  1721 
    Google Scholar
  • 11a Legeay JC. Lewis W. Stockman RA. Chem. Commun.  2009,  2207 
    Google Scholar
  • 11b Diaz-Gavilan M. Galloway WRJD. O’Connell KMG. Hodkingson JT. Spring DR. Chem. Commun.  2010,  46:  776 
    Google Scholar
  • 12 DeSousa R. Thurier C. Len C. Pouilloux Y. Barrault J. Jerome F. Green Chem.  2011,  13:  1129 
    Google Scholar
  • 13a Braun RA. J. Org. Chem.  1963,  28:  1383 
    Google Scholar
  • 13b Trost BM. Aponick A. J. Am. Chem. Soc.  2006,  128:  3931 
    Google Scholar
  • 13c Hekmatshoar R. Yavari I. Beheshtiha YS. Heravi MM. Monatsh. Chem.  2001,  132:  689 
    Google Scholar
  • 14 Chollet A.-M. Le Diguarher T. Kucharczyk N. Loynel A. Bertrand M. Tucker G. Guilbaud N. Burbridge M. Pastoureau P. Fradin A. Sabatini M. Fauchère J.-L. Casara P. Bioorg. Med. Chem.  2002,  10:  531 
    Google Scholar
  • 15a Schmidt B. Kunz O. Biernat A. J. Org. Chem.  2010,  75:  2389 
    Google Scholar
  • 15b Schmidt B. Geißler D. ChemCatChem  2010,  2:  423 
    Google Scholar
  • 15c Wang Y. Dai WM. Tetrahedron  2010,  66:  187 
    Google Scholar
  • 15d Perepogu AK. Raman D. Murty USN. Rao VJ. Synth. Commun.  2010,  40:  686 
    Google Scholar
  • 15e Michaelis S. Blechert S. Org. Lett.  2005,  24:  5513 
    Google Scholar
  • 15f Crimmins MT. Jacobs DL. Org. Lett.  2009,  11:  2695 
    Google Scholar
  • 15g Selvakumar N. Kumar PK. Reddy KCS. Chary BC. Tetrahedron Lett.  2007,  48:  2021 
    Google Scholar
  • 15h Ghosh AK. Cappiello J. Shin D. Tetrahedron Lett.  1998,  39:  4651 
    Google Scholar
  • 15i Ewing D. Glaçon V. Mackenzie G. Postel D. Len C. Tetrahedron Lett.  2002,  43:  3503 
    Google Scholar
  • 15j Ewing D. Glaçon V. Mackenzie G. Postel D. Len C. Tetrahedron  2003,  59:  941 
    Google Scholar
  • 15k Rodriguez-Fernandez MM. Vuong S. Renoux B. Len C. Synlett  2007,  1703 
    Google Scholar
  • 15l Vuong S. Rodriguez-Fernandez MM. Renoux B. Len C. Carbohydr. Res.  2010,  345:  324 
    Google Scholar