Categories: Synthesis of O-Heterocycles, C-O Bond Formation >
Synthesis of butenolides
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Recent Literature
Various α-substituted butenolides were efficiently
prepared from 3-bromo-2-triisopropylsilyloxyfuran via
lithium-bromine exchange and subsequent derivatization with carbon
or heteroatom electrophiles. A short and efficient synthesis of an anti-inflammatory lipid,
isolated from a marine gorgonian, is described.
J. Boukouvalas, R. P. Loach, J. Org. Chem., 2008,
73, 8109-8112.
4-tosyl-2(5H)-furanone is easy to prepare in excellent yield and more stable than
the corresponding triflate. A palladium
catalyzed reaction between 4-tosyl-2(5H)-furanone and boronic acids gives 4-substituted 2(5H)-furanones.
J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem., 2003, 68, 670-673.
The mild, palladium-catalyzed reaction of arenediazonium tetrafluoroborates with
methyl 4-hydroxy-2-butenoate in MeOH gives 4-arylbutenolides in good yields
through a domino vinylic substitution/cyclization process. The reaction
tolerates halogen substituents, nitro, ether, cyano, keto, and ester groups and
can be performed as a one-pot process generating the arenediazonium salt in situ.
S. Cacchi, G. Fabrizi, A. Goggiamani, A. Sferrazza, Synlett, 2009,
1277-1280.
The ruthenium-catalyzed
ring-closing metathesis of methallyl acrylates gave 4-Methyl-5-alkyl-2(5H)-furanones
in good to high yields. Despite the electron deficiency of both double bonds in
the starting acrylates, the first-generation
Grubbs' catalyst proved to be an effective catalyst for the ring closure.
M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Org. Lett., 2005, 7, 1805-1808.
A Pd-catalyzed arylation of butenolides with high selectivity for the γ-position
allows a facile construction of quaternary centers. The preparation of a wide
variety of γ-aryl butenolides containing a number of functional groups is
outlined.
A. M. Hyde, S. L. Buchwald, Org. Lett., 2009,
11, 2663-2666.
A new and convenient one-pot catalytic addition-elimination reaction converted a
range of (E)-3-butenoic acids into the corresponding butenolides in good
yields in the presence of 5 mol % diphenyl diselenide and [bis(trifluoroacetoxy)iodo]benzene
in acetonitrile.
D. M. Browne, O. Niyomura, T. Wirth, Org. Lett., 2007,
9, 3169-3171.
A Cu(II)-catalyzed acylation of acyloins with a thiol ester present in Wittig
reagents under neutral conditions through a push-pull mechanism enables a
one-pot lactonization to yield butenolides. The synthetic utility of this method
for the synthesis of natural products is shown.
K. Matuso, M. Shindo, Org. Lett., 2010,
12, 5346-5349.
A sequential rhodium-catalyzed addition/lactonization reaction of organoboron
derivatives to alkyl 4-hydroxy-2-alkynoates allows the synthesis of 4-aryl/heteroaryl/vinyl-2(5H)-furanones
with an excellent control of regio- and chemoselectivity.
M. Alfonsi, A. Arcadi, M. Chiarini, F. Marinelli, J. Org. Chem., 2007,
72, 9510-9517.
A boron-catalyzed aldol reaction of pyruvic acids with aldehydes in water at
room temperature delivers useful isotetronic acid derivatives in high yields.
Both boronic and borinic acids function as catalysts, with the latter
demonstrating particularly high activity. A wide range of aldehydes, including
enolizable species, may be employed.
D. Lee, S. G. Newman, M. S. Taylor, Org. Lett., 2009,
11, 5486-5489.
Tetronic acids substituted by various groups were synthesized in one pot from
the corresponding aryl- or heteroarylacetic acid esters and hydroxyacetic acid
esters, by a tandem process involving a transesterification and a subsequent
Dieckmann cyclization.
A. Mallinger, T. Le Gall, C. Mioskowski, Synlett, 2008,
386-388.
A one-pot, convenient and general access to 5-sp2-substituted and
5,5-disubstituted tetronic acids embodies two consecutive chemical events: a
Michael addition of pyrrolidine on a secondary or tertiary γ-hydroxy-α,β-alkynyl
ester derivative to give the corresponding enamine, and a subsequent
acid-catalyzed hydrolysis-lactonization.
D. Tejedor, A. Santos-Expósito, F. García-Tellado, Synlett, 2006,
1607-1609.
A highly efficient carbon-carbon triple bond cleavage reaction of (Z)-enynols
offered a new route to highly substituted butenolides through a
gold(I)-catalyzed tandem cyclization/oxidative cleavage.
Y. Liu, F. Song, S. Guo, J. Am. Chem. Soc., 2006, 128, 11332-11333.
γ-Methylene-α,β-unsaturated γ-lactones were efficiently synthesized by a
Pd-catalyzed cyclization of 3,4-alkadienoic acids. The use of a N2
atmosphere ensures a high purity of the products.
S. Ma, F. Yu, Tetrahedron, 2005,
61, 9896-9901.
The facile iodolactonisation of ethyl 2,3-allenoates with I2 in aqueous MeCN
gave 4-iodofuran-2(5H)-ones in moderate to
high yields.
C. Fu, S. Ma, Eur. J. Org. Chem., 2005,
3942-3945.
A biomimetic proton transfer catalysis with a chiral organic catalyst enabled an
enantioselective olefin isomerization of a broad range of mono- and
disubstituted β,γ-unsaturated butenolides into the corresponding chiral
α,β-unsaturated butenolides in high enantioselectivity and yield. Mechanistic
studies have revealed the protonation as the rate-determining step.
Y. Wu, R. P. Singh, L. Deng, J. Am. Chem. Soc., 2011,
133, 12458-12461.
