22122-36-7Relevant articles and documents
A novel and convenient synthesis of 3-methylfuran-2(5H)-one
Nefkens, Gerard H.L.,Thuring, Jan Willem J.F.,Zwanenburg, Binne
, p. 290 - 292 (1997)
3-Methylfuran-2(5H)-one (1a), a precursor of strigol and its analogues, is prepared in a highly efficient manner by a regiocontrolled alcoholysis of citraconic anhydride and subsequent reduction via the mixed anhydride 5c.
An efficient and short synthesis of 3-methyl-2(5H)-furanone, a synthon for strigol analogues
Mangnus,Zwanenburg
, p. 783 - 786 (1992)
A three steps synthesis of 3-methyl-2(5H)-furanone from citraconic anhydride is reported. The furanone is prepared in an overall yield of 60%.
A New Synthesis of Substituted Butenolides via Cation-Initiated Ring Expansion/Elimination of β-Lactones
Black, T. Howard,Huang, Jianhua
, p. 1411 - 1412 (1993)
When treated with silver ion, γ-bromo β-lactones, available via bromolactonization, undergo a ring expansion/elimination reaction to afford substituted butenolides.
A new expedient synthesis of 3-methyl-2(5 H)-furanone, the common substructure in strigolactones, and its proposed biosynthesis
Malik, Heetika,Rutjes, Floris P. J. T.,Zwanenburg, Binne
, p. 3271 - 3273 (2010)
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. Georg Thieme Verlag Stuttgart New York.
Butenolide synthesis from functionalized cyclopropenones
Nguyen, Sean S.,Ferreira, Andrew J.,Long, Zane G.,Heiss, Tyler K.,Dorn, Robert S.,Row, R. David,Prescher, Jennifer A.
, p. 8695 - 8699 (2019/10/28)
A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
The bioinspired design of a reagent allows the functionalization of Cα-H of α,β-unsaturated carbonyl compounds via the Baylis-Hillman chemistry under ambient conditions
Singh, Palwinder,Kumar, Arun,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Harpreet
supporting information, p. 2936 - 2939 (2016/02/20)
A rationally designed reagent capable of affecting alkylation at Cα of α,β-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-bond formation during the reaction play a key role in the working of the reagent.
