- Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound
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Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.
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Paragraph 0303; 0308-0310
(2020/09/17)
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- Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C
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An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results.
- Tian, Guilong,Fedoseev, Pavel,Van der Eycken, Erik V.
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supporting information
p. 5224 - 5227
(2017/04/24)
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- Design and synthesis of neolamellarin a derivatives targeting heat shock protein 90
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In this study, we designed and synthesized a novel family of neolamellarin A derivatives that showed high inhibitory activity toward heat shock protein 90 (Hsp90), a kinase associated with cell proliferation. The 3,4-bis(catechol)pyrrole scaffold and the benzyl group with methoxy modification at N position of pyrrole are essential to the Hsp90 inhibitory activity and cytotoxicity of these compounds. Western blot analysis demonstrated that these compounds induced dramatic depletion of the examined client proteins of Hsp90, and accelerated cancer cell apoptosis. Docking simulations suggested that the binding mode of 9p was similar to that of the VER49009, a potent inhibitor of Hsp90. Further molecular dynamics simulation indicated that the hydrophobic interactions as well as the hydrogen bonds contributed to the high affinity of 9p to Hsp90.
- Jiang, Long,Yin, Ruijuan,Wang, Xueting,Dai, Jiajia,Li, Jing,Jiang, Tao,Yu, Rilei
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supporting information
p. 24 - 33
(2017/04/21)
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- Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
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(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.
- Ruiz-Olalla, Andrea,Würdemann, Martien A.,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk
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p. 5125 - 5132
(2015/05/27)
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- C-H alkenylation of azoles with enols and esters by nickel catalysis
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Rather u(Ni)que: Two new C-H alkenylation reactions, that is C-H/Ci£O alkenylation and decarbonylative C-H alkenylation, of azoles are uniquely catalyzed by Ni/dcype. These azole alkenylation reactions are successfully applied to the convergent formal synthesis of siphonazoleB.
- Meng, Lingkui,Kamada, Yuko,Muto, Kei,Yamaguchi, Junichiro,Itami, Kenichiro
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supporting information
p. 10048 - 10051
(2013/10/01)
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- o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol
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A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.
- Gharpure, Santosh J.,Sathiyanarayanan,Jonnalagadda, Prasad
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p. 2974 - 2978
(2008/09/20)
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- PHENYLALKANOL COMPOUNDS
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The present invention relates to phenylalkanol compounds of formula (I) and derivatives, prodrugs, isomers and/or tautomers thereof. The present invention also relates to processes for the preparation of a compound of formula (I) and their use as pharmaceutical or veterinary agents, in particular as modulators of the vanilloid receptor for the treatment and/or prophylaxis of pain.
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Page/Page column 30
(2010/11/25)
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- A unified strategy for the synthesis of phenanthroizidine alkaloids: Preparation of sterically congested pyridines
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Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe
- Ciufolini, Marco A.,Roschangar, Frank
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p. 12082 - 12089
(2007/10/03)
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- TOTAL SYNTHESIS OF (+/-)-HYDRANGENOL
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The title compound 8 has been synthesized in five steps and in about 33percent overall yield from 3-methoxyphenylacetic acid, 1.Acid 1 was condensed with anisole in polyphosphoric acid to give 3',4-dimethoxydeoxybenzoin, 2, which was converted to the ethylene acetal 3.The latter was metallated with buthyllithium and carbonated giving crude 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid, 4, from which 3,4-dihydro-8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 7, was obtained either by reduction with sodium borohydride and dehydration, or dehydration to 8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 6, and catalytic hydrogenation.Finally, demethylation of 6 to 8 was performed with boron tribromide.
- Napolitano, Elio,Ramacciotti, Antonella,Fiaschi, Rita
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p. 101 - 104
(2007/10/02)
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