Download PDF
Synthesis 2010(19): 3271-3273  
DOI: 10.1055/s-0030-1257911
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Expedient Synthesis of 3-Methyl-2(5H)-furanone, the Common Substructure in Strigolactones, and Its Proposed Biosynthesis

Heetika Malik, Floris P. J. T. Rutjes*, Binne Zwanenburg*
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
Fax: +31(24)3653393; e-Mail: b.zwanenburg@science.ru.nl;
Further Information

Publication History

Received 27 March 2010
Publication Date:
30 July 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

3-Methyl-2(5H)-furanone is the common structural unit in natural and several synthetic strigolactones, which are germination stimulants for seeds of the parasitic weeds Striga and Orobanche spp. A simple, one-step, ring-closing metathesis of allyl methacrylate using an appropriate Grubbs catalyst gives this fur­anone in good yield. Acid-catalyzed condensation of glyoxal and methylmalonic acid gives 5-hydroxy-3-methyl-2(5H)-furanone, which is another synthon for the introduction of the furanone unit into strigolactones. In addition, a biosynthetic pathway is presented for the incorporation of the furanone unit into strigolactones, which is relevant in view of the current interest in the newly discovered ­biological functions of strigolactones.

Key words

ring-closing metathesis - Grubbs catalyst - allyl methacrylate - strigolactones - aldol condensation - biosynthesis

    References

  • 1 Parker C. Pest Manag. Sci.  2009,  65:  453 ; and references cited therein
    CrossrefGoogle Scholar
  • 2a Cook CE. Whichard LP. Wall ME. Egley GH. Coggon P. Luhan PA. McPhail AT. J. Am. Chem. Soc.  1972,  94:  6198 
    Google Scholar
  • 2b Yoneyama K. Xie X. Yoneyama K. Takeuchi Y. Pest Manag. Sci.  2009,  65:  467 ; and references cited therein
    Google Scholar
  • 3 Zwanenburg B. Mwakaboko AS. Reizelman A. Anilkumar G. Sethumadhavan D. Pest Manag. Sci.  2009,  65:  478 
    CrossrefGoogle Scholar
  • 4 Thuring JWJF. Bitter HH. de Kok MMK. Nefkens GHL. van Riel AMDA. Zwanenburg B.
    J. Agric. Food Chem.  1997,  45:  2273 
    CrossrefGoogle Scholar
  • 5 Johnson AW. Gowda G. Hassanali A. Knox J. Monaco S. Razawi Z. Roseberry G. J. Chem. Soc., Perkin Trans. 1  1981,  1734 
    CrossrefGoogle Scholar
  • 6 Mangnus EM. Dommerholt FJ. de Jong RLP. Zwanenburg B. J. Agric. Food Chem.  1992,  40:  1230 
    CrossrefGoogle Scholar
  • 7 Cooper GK. Dolby LJ. J. Org. Chem.  1979,  44:  3414 
    CrossrefGoogle Scholar
  • 8 Mangnus EM. Zwanenburg B. Synth. Commun.  1992,  22:  783 
    CrossrefGoogle Scholar
  • 9 Nefkens GHJ. Thuring JWJF. Zwanenburg B. Synthesis  1997,  290 
    Article in Thieme ConnectGoogle Scholar
  • 10a Stewart IC. Ung T. Plenev AA. Berlin JM. Grubbs RH. Schrodi Y. Org. Lett.  2007,  9:  1589 
    Google Scholar
  • 10b Schrodi Y. Pederson RL. Aldrichimica Acta  2007,  40:  45 
    Google Scholar
  • 11 Furstner A. Dierkes T. Org. Lett.  2000,  2:  2463 
    CrossrefGoogle Scholar
  • 12 Burness DM. Org. Synth.  1959,  36:  46 
    Google Scholar
  • 13 Rani K. Zwanenburg B. Sugimoto Y. Yoneyama K. Bouwmeester HJ. Plant Physiol. Biochem.  2008,  46:  617 
    CrossrefGoogle Scholar
  • 14a Tsuchiya Y. McCourt P. Curr. Opin. Plant Biol.  2009,  12:  556 
    Google Scholar
  • 14b Bouwmeester HJ. Roux C. Lopez-Raez JA. Bécard G. Trends Plant Sci.  2007,  12:  224 
    Google Scholar
  • 15 Ichihara A. Nio N. Terayama Y. Kimura R. Sakamura S. Tetrahedron Lett.  1979,  3731 
    CrossrefGoogle Scholar