149694-49-5Relevant academic research and scientific papers
Efficient synthesis of furan-2-ylacetates, 7-(alkoxycarbonyl)benzofurans, and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans based on cyclization reactions of free and masked dianions: A "cyclization/dehydrogenation" strategy
Bellur, Esen,Langer, Peter
, p. 10013 - 10029 (2005)
A variety of furan-2-ylacetates have been prepared by dehydrogenation of monocyclic 2-alkylidene-tetrahydrofurans, which are readily available by cyclizations of open-chained 1,3-dicarbonyl dianions with 1-bromo-2- chloroethane. 5′H-[2,3′]Bifuranyl-2′-one
Synthesis of functionalized furans based on a '[3+2] cyclization/ bromination/elimination' strategy
Bellur, Esen,Langer, Peter
, p. 480 - 488 (2006)
The bromination of 2-alkylidenetetrahydrofurans - readily available via one-pot [3+2] cyclizations - afforded 2-alkylidene-3-bromotetrahydrofurans. Elimination of hydrogen bromide and subsequent aromatization of these compounds provided a convenient appro
Efficient synthesis of functionalized furans and benzofurans based on a '[3+2] cyclization/oxidation' strategy
Bellur, Esen,Freifeld, Ilia,Langer, Peter
, p. 2185 - 2187 (2005)
Functionalized furans and benzofurans were prepared by DDQ oxidation of 2-alkylidenetetrahydrofurans, which are readily available by one-pot cyclizations of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers.
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
supporting information, p. 8874 - 8881 (2021/03/17)
Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
Regioselective synthesis of functionalized furans by cyclization of 1,3-bis-silyl enol ethers with 1-chloro-2,2-dimethoxyethane
Bellur, Esen,Goerls, Helmar,Langer, Peter
, p. 2074 - 2090 (2007/10/03)
Cyclization of 1,3-bis-silyl enol ethers with 1-chloro-2,2-dimethoxyethane allowed an efficient, regio- and diastereo-selective synthesis of a variety of 2-alkylidene-4-methoxy-tetrahydrofurans. The TFA-mediated elimination of methanol resulted in the formation of functionalized furans. Simi larly, 2,3,3a,4,5,6-hexahydro-2,3-benzofurans were prepared and transformed into 4,5,6,7-tetrahydro-2,3-benzofurans by treatment with TFA Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-En-4-yn-l-ols
Gabriele, Bartolo,Salerno, Giuseppe,De Pascali, Francesca,Costa, Mirco,Chiusoli, Gian Paolo
, p. 7693 - 7699 (2007/10/03)
A variety of (Z)-2-en-4-yn-l-ols have been carbonylated under oxidative conditions to give substituted furan-2-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 °C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (￡)-2-[(alkoxycarbonyl)methylene]-2, 5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.
Carbonylation of Alkynyl Epoxides: Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives
Piotti, Marcelo E.,Alper, Howard
, p. 8484 - 8489 (2007/10/03)
The carbonylation of alkynyl oxiranes catalyzed by (MePh2)4Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethano
Novel synthesis of furan-2-acetic esters by palladium-catalysed oxidative cyclization-alkoxycarbonylation of (Z)-2-En-4-yn-1-ols
Gabriele, Bartolo,Salerno, Giuseppe,De Pascali, Francesca,Sciano, Giuseppe Tomasi,Costa, Mirco,Chiusoli, Gian Paolo
, p. 6877 - 6880 (2007/10/03)
Furan-2-acetic esters are obtained in good yields by direct oxidative cyclization-alkoxycarbonylation lation of (Z)-2-en-4-yn-1-ols. bearing both an alkyl or an aryl substituent a to the hydroxy group. in the presence of catalytic amounts of palladium iod
Synthesis of Rosefuran. A New Route to Furans through Base-Catalyzed Cyclization of Hydroxy Alkynoates and Alkynones
Marshall, James A.,DuBay, William J.
, p. 3602 - 3603 (2007/10/02)
A new synthesis of furans involving intramolecular 1,4-addition of (Z)-6-hydroxy 4-en-2-ynoates and ynones has been developed and applied to a total synthesis of rosefuran.
