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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;
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Publication History

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

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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