183488-93-9Relevant academic research and scientific papers
General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory Gorgonian lipid
Boukouvalas, John,Loach, Richard P.
, p. 8109 - 8112 (2008/12/22)
(Chemical Equation Presented) A variety of α-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.
Efficient preparation of 3-substituted-furan-2(5H)-ones and their direct vinylogous aldol addition
Bella, Marco,Piancatelli, Giovanni,Squarcia, Antonella
, p. 4429 - 4436 (2007/10/03)
The deprotonation of 3-substituted-furan-2(5H)-ones 1, obtained via the hydrolysis of 3-substituted-2,5-dihydro-2,5-dimethoxyfurans, affords in the reaction with both aromatic and aliphatic aldehydes regioselectively the unsaturated 3-substituted 5-(1′-hydroxy)-γ-butyrolactones, such as 4, 5, 6, 7, 8, 9 and 10. The use of Lewis acids allows modulation of the diastereoisomeric ratios. The subsequent reduction, carried out with nickel boride, gives rise to the formation of the corresponding saturated 5-(1′-hydroxy)-γ-butyrolactones, such as 11, 12 and 13.
3-Phenylselanylfuran-2(5H)-one: A versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones
Bella, Marco,Piancatelli, Giovanni,Pigro, Maria Cristina
, p. 12387 - 12398 (2007/10/03)
Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ- butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.
Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones
Hollingworth, Gregory J.,Perkins, Gemma,Sweeney, Joseph
, p. 1913 - 1919 (2007/10/03)
Stannylfuranones 1 and 2 were prepared by ipso radical desulfurative stannylation of phenylsulfanylfuranones 3 and 16. Compounds 1 and 2 underwent Stille coupling reactions with aryl iodides to give 3- and 4-arylfuran-2(5H)-ones.
