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

doi:10.1055/s-0030-1257911

SHORTPAPER

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;

Abstract

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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

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