75135-41-0Relevant academic research and scientific papers
Synthesis and biological evaluation of furano-epothilone C
Schinzer, Dieter,B?hm, Oliver M.,Altmann, Karl-Heinz,Wartmann, Markus
, p. 1375 - 1378 (2004)
An efficient synthesis of furano-epothilone C (1) is described by the use of an aldol reaction and a ring-closing metathesis (RCM) for the closure of the macrocyclic ring system. This new type of analog contains a furan ring in the C8-C10 region of the macrocycle. The biology of this new class of epothilone C analog has been studied.
Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols
Albarrán-Velo, Jesús,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 4096 - 4108 (2021/08/19)
The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).
An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5
Breunig, Michael,Gaich, Tanja,Yuan, Po
supporting information, p. 5521 - 5525 (2020/02/20)
We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. Ring-closing metathesis and an auxiliary-directed 1,4-addition are the key steps of our synthetic route. During the synthesis, an unprecede
MIDA boronate allylation-synthesis of ibuprofen
Brodie, Glen,France, David J.,Memarzadeh, Sarah,Phillips, David,Tang, Gi Lum
, p. 30624 - 30630 (2020/09/11)
MIDA boronates are among the most useful reagents for the Suzuki-Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen. This journal is
Manganese catalyzed dehydrogenative silylation of alkenes: Direct access to allylsilanes
Wu, Shang,Zhang, Ying,Jiang, Hongyan,Ding, Ning,Wang, Yanbin,Su, Qiong,Zhang, Hong,Wu, Lan,Yang, Quanlu
supporting information, (2020/06/03)
Dehydrogenative silylation of alkenes with silanes to produce allylsilanes is achieved through manganese catalysis with a wide scope of substrate tolerance. This transformation involves silane radicals initiated by manganese complex without additional oxidant additives. It offers a general, convenient and practical protocol with excellent functional group compatibility and gram-scale capacity for the modular synthesis of allylsilanes.
Production of α - olefin having a furan ring (by machine translation)
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Paragraph 0044, (2018/09/11)
[Problem] to provide, relatively inexpensive material having a high versatility from the furan ring in high yield production of novel α - olefin. [Solution] (2) Production of olefins having formula represented by α - furan ring, (1) the formula represente
Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen
Chen, Huoji,Yang, Wanfei,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 3340 - 3343 (2014/05/20)
A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile. the Partner Organisations 2014.
Biocatalytic cleavage of alkenes with O2 and Trametes hirsuta G FCC 047
Lara, Miguel,Mutti, Francesco G.,Glueck, Silvia M.,Kroutil, Wolfgang
supporting information; experimental part, p. 3668 - 3672 (2009/05/07)
Alkenes possessing a C=C double bond adjacent to an aromatic ring were cleaved to yield the corresponding carbonyl compounds by use of molecular oxygen as the sole oxidant and a cell-free extract of the wood-degrading fungus Trametes hirsuta FCC 047 as catalyst. The oxygen pressure required was optimized. Special adapted equipment allowed 96 reactions to be performed in parallel under controlled oxygen pressure. A broad spectrum of aryl-alkenes was successfully converted into the corresponding ketones/aldehydes with excellent chemoselectivity under a controlled oxygen atmosphere (2 bar). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
ARYLINDENOPYRIDINES AND ARYLINDENOPYRIDINES AND THEIR USE AS ADENOSINE A2A RECEPTOR ANTAGONIST
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Page/Page column 23, (2008/06/13)
This invention provides novel arylindenopyridines and arylindenopyrimidines of formula (I), (II) wherein R1, R2, R3, R4, and X are as defined above, and pharmaceutical compositions comprising same, useful for tr
Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
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, (2008/06/13)
This invention provides novel arylindenopyridines and arylindenopyrimidines of the formula: wherein R1, R2, R3, R4, and X are as defined above, and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by antagonizing adenosine A2a receptors. This invention also provides therapeutic and prophylactic methods using the instant compounds and pharmaceutical compositions.
