66088-37-7Relevant academic research and scientific papers
Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (-)-Longirabdolactone, and (-)-Effusin
Zhang, Jianpeng,Li, Zijian,Zhuo, Junming,Cui, Yue,Han, Ting,Li, Chao
supporting information, p. 8372 - 8380 (2019/06/10)
Structurally complex and bioactive ent-kaurane diterpenoids have well-characterized biological functions and have drawn widespread attention from chemists for many decades. However, construction of highly oxidized forms of such diterpenoids still presents considerable challenges to synthetic chemists. Herein, we report the first total syntheses of C19 oxygenated spiro-lactone ent-kauranoids, including longirabdiol, longirabdolactone, and effusin. A concise synthesis of the common intermediate used for all three syntheses was enabled via three free-radical-based reactions: (1) a newly devised tandem decarboxylative cyclization/alkenylation sequence that forges the cis-19, 6-lactone concomitantly with vicinal alkenylation, (2) a Ni-catalyzed decarboxylative Giese reaction that constructs C10 quaternary center stereoselectively, and (3) a vinyl radical cyclization that generates a rigid bicyclo[3.2.1]octane. A series of late-stage oxidations from the common intermediate then provided each of the natural products in turn. Further biological evaluation of these synthetic natural products reveals broad anticancer activities.
Catalytic allylic oxidation to generate vinylogous acyl sulfonates from vinyl sulfonates
Tucker, James K.,Shair, Matthew D.
supporting information, p. 2473 - 2476 (2019/03/29)
Regioselective formation of vinylogous acyl sulfonates was accomplished via the allylic oxidation of the corresponding vinyl sulfonates. The reaction progressed through the agency of catalytic iron(III) chloride catalysis with tert-Butyl hydroperoxide (TBHP) as the stoichiometric oxidant. Tolerance of other functional groups, including some other allylic and benzylic sites, was observed.
Does the Exception Prove the Rule? A Comparative Study of Supramolecular Synthons in a Series of Lactam Esters
Weck,Nauha,Gruber
, p. 2899 - 2911 (2019/05/10)
In this paper a series of simple lactam esters and carboxylic acids is studied with respect to their overall conformation and hydrogen bonding patterns. In total, eight lactams featuring Nα-substitution have been synthesized. Additionally, the molecular structures of related lactam esters have been considered. The length of the amide bonds does not seem to be majorly influenced by different substituents unless the electron withdrawing N-Boc-protection group is introduced, resulting in a higher susceptibility toward hydrolytic ring opening. As known from other lactams, the Nα ester moiety of the title compounds can be in an axial or equatorial conformation. Smaller ester groups were found to prefer equatorial positions, while larger ones occupy axial sites. N-substitution seems to promote axial conformations of the respective Nα group, with enantholactams being the only studied exception. In addition to the two common amide packing motifs, i.e., the R2 2 (8) amide dimer (NH···O/NH···O) and the C(4) amide chain, a third graph-set was found: the R2 2(8) NH···O/CH···O=C heterodimer. In general, there seems to be a tendency for medium-sized lactams as well as lactams with small esters to form R2 2 (8) amide dimers. Larger esters and enantholactam esters lead to C(4) amide chains. In this respect the formation of R2 2(8) N - H···O/C-H···O=C heterodimers should be seen as a remarkable exception.
HIGHLY DIASTEREOSELECTIVE CONSTRUCTION OF THE 4,5-SPIROCYCLE VIA PALLADIUM-CATALYZED INTRAMOLECULAR ALKENYLATION
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Page/Page column 66, (2018/12/13)
A diastereoselective method of preparing benzofuran-based 4,5-spirocycles via metal catalyzed alkenylation is described. The method can be used to provide compounds containing the benzofuranone-4,5-spirocyclic motif of the phainanoids, a class a natural p
Total Synthesis of (±)-Waihoensene
Lee, Hongsoo,Kang, Taek,Lee, Hee-Yoon
supporting information, p. 8254 - 8257 (2017/06/30)
The first total synthesis of waihoensene, a tetracyclic diterpene containing an angular triquinane and a six-membered ring, with four contiguous quaternary carbon atoms, was achieved through the tandem cycloaddition reaction of an allenyl diazo substrate containing a six-membered ring via trimethylenemethane (TMM) diyl intermediate.
Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation
Xie, Jiaxin,Wang, Jianchun,Dong, Guangbin
supporting information, p. 3017 - 3020 (2017/06/07)
An efficient strategy to synthesize the western part of phainanoids is reported. The benzofuranone-based 4,5-spirocyclic motif is constructed diastereoselectively via a palladium-catalyzed intramolecular alkenylation. The computational study suggests that
N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions
Blümel, Marcus,Crocker, Reece D.,Harper, Jason B.,Enders, Dieter,Nguyen, Thanh V.
supporting information, p. 7958 - 7961 (2016/07/06)
N-Heterocyclic olefins (NHOs) have very recently emerged as efficient promoters for several chemical reactions due to their strong Br?nsted/Lewis basicities. Here we report the novel application of NHOs as efficient phase-transfer organocatalysts for synt
Inhibitors of influenza viruses replication
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Page/Page column 347; 348, (2016/06/14)
Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A compound is represented by Structural Formula (IA) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS
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Page/Page column 686, (2015/02/02)
The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.
INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Paragraph 0916, (2016/10/08)
PROBLEM TO BE SOLVED: To provide inhibitors of influenza virus replication. SOLUTION: Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient comprise administering to the biological sample or patient an effective amount of a compound represented by structural formula (I) or a pharmaceutically acceptable salt thereof, where the values of structural formula (IA) are as described herein. A compound is represented by structural formula (IA) or a pharmaceutically acceptable salt thereof, where the values of structural formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle. COPYRIGHT: (C)2015,JPO&INPIT
