22601-06-5Relevant academic research and scientific papers
The synthesis of (+)-nemorensic acid
Donohoe, Timothy J.,Guillermin, Jean-Baptiste,Frampton, Christopher,Walter, Daryl S.
, p. 465 - 466 (2000)
The synthesis of (+)-nemorensic acid in nine steps is described; key steps in the route were the stereoselective Birch reduction of a substituted furan, and addition of allyltrimethylsilane to an oxonium ion at C-5; an X- ray crystal structure of (-)-nemorensic acid provided proof of the relative stereochemistry of the target.
The synthesis of (-)-cis- and (-)-trans-crobarbatic acid
Donohoe, Timothy J.,Stevenson, Clare A.,Helliwell, Madeleine,Irshad, Ranah,Ladduwahetty, Tamara
, p. 1315 - 1322 (1999)
The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid.
A new simple route to furanic ketones; preparation of elsholtzione naginata ketone and perilla ketone
Cahiez,Chavant,Metais
, p. 5245 - 5248 (1992)
Copper- or iron-catalyzed acylation of organomanganese reagents allows to obtain 3- and 2-acylfurans in high yields. Elsholtzione, naginata ketone and perilla ketone have been prepared according to this procedure.
Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction
Li, Xiang,Zhou, Bo,Yang, Run-Ze,Yang, Fu-Ming,Liang, Ren-Xiao,Liu, Ren-Rong,Jia, Yi-Xia
supporting information, p. 13945 - 13951 (2018/10/20)
Enantioselective intramolecular dearomative Heck reactions have been developed by Pd-catalyzed cross-coupling of aryl halides or aryl triflates with the internal C=C bond of indoles, benzofurans, pyrroles, and furans. A variety of structurally unique spir
Pd(II)-Catalyzed Arylation and Intramolecular Amidation of γ-C(sp3)-H Bonds: En Route to Arylheteroarylmethane and Pyrrolidone Ring Annulated Furan/Thiophene Scaffolds
Parella, Ramarao,Babu, Srinivasarao Arulananda
, p. 7123 - 7150 (2017/07/26)
We report the Pd(II)-catalyzed, bidentate directing group (BDG)-assisted arylation and successive arylation/intramolecular amidation of γ-C(sp3)-H bonds. The Pd(II)-catalyzed BDG-assisted C-H activation and functionalization of the β-C(sp3)-H bonds of carboxylic acids are well documented, but only a few reports are available that deal with the BDG-directed functionalization of the γ-C(sp3)-H bonds. Various 3-methylthiophene/furan-2-carboxamides (1a-e) were derived from their corresponding carboxylic acids and bidentate directing groups. These compounds were then used as substrates to investigate the arylation and successive arylation/intramolecular amidation of the γ-C(sp3)-H bonds. The γ-C(sp3)-H arylation arose from the Pd(II)-catalyzed reactions of these compounds with aryl iodides with reaction periods of 4-24 h (except a few reactions which required 36 or 48 h). Notably, these reactions led to the construction of various unsymmetrical diarylmethane scaffolds, such as thiophene/furan-based arylheteroarylmethanes (3-6). Prolonging the reaction period to 48-70 h led to successive γ-C(sp3)-H arylation/intramolecular amidation and the construction of both C-C and C-N bonds. Accordingly, these reactions led to the construction of new classes of pyrrolidone-ring annulated thiophene/furan-based heterocyclic scaffolds (e.g., 4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-ones (8), 4,5-dihydro-6H-furo[2,3-c]pyrrol-6-ones (10), and 1-phenyl-1,2-dihydro-3H-benzo[4,5]thieno[2,3-c]pyrrol-3-ones (12)), and notably, compounds 8, 10, and 12 resemble the skeletons of 3-phenylisoindolin-1-ones.
Conformational effects in diastereoselective aryne diels-alder reactions: synthesis of benzo-fused [2.2.1] heterobicycles
Webster, Robert,Lautens, Mark
supporting information; experimental part, p. 4688 - 4691 (2009/12/26)
It was found that the diastereoselectivity of the Dials-Alder reaction between arynes and substituted furans Is highly sensitive to substitution, which affects the reactive conformation. By varying the location of the groups on the diene partner, It Is po
SULFOXIMINES AS KINASE INHIBITORS
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Page/Page column 73, (2008/12/05)
The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.
Kinase Inhibitors
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Page/Page column 155, (2008/06/13)
The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.
Synthesis and biological activity of novel 4,4-difluorobenzazepine derivatives as non-peptide antagonists of the arginine vasopressin V 1A receptor
Shimada, Yoshiaki,Taniguchi, Nobuaki,Matsuhisa, Akira,Akane, Hiroaki,Kawano, Noriyuki,Suzuki, Takeshi,Tobe, Takahiko,Kakefuda, Akio,Yatsu, Takeyuki,Tahara, Atsuo,Tomura, Yuichi,Kusayama, Toshiyuki,Wada, Koh-Ichi,Tsukada, Junko,Orita, Masaya,Tsunoda, Takashi,Tanaka, Akihiro
, p. 1827 - 1837 (2007/10/03)
To find potent and selective antagonists of the arginine vasopressin (AVP) V1A receptor, optimization studies of compounds structurally related to (Z)-N-{4′-[(4,4-difluoro-5-carbamoylmethylidene-2,3,4,5-tetrahydro-1H- 1-benzazepin-1-yl)carbonyl
Synthesis of Enantiopure Dihydropyranones: Aldol-Based Ring Expansion of Dihydrofurans
Donohoe, Timothy J.,Raoof, Ali,Freestone, Graeme C.,Linney, Ian D.,Cowley, Andrew,Helliwell, Madeleine
, p. 3059 - 3062 (2007/10/03)
(Matrix Presented) The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functio
