88159-06-2Relevant articles and documents
Click, Release, and Fluoresce: A Chemical Strategy for a Cascade Prodrug System for Codelivery of Carbon Monoxide, a Drug Payload, and a Fluorescent Reporter
De La Cruz, Ladie Kimberly C.,Benoit, Stéphane L.,Pan, Zhixiang,Yu, Bingchen,Maier, Robert J.,Ji, Xingyue,Wang, Binghe
, p. 897 - 900 (2018)
A chemical strategy was developed wherein a single trigger sets in motion a three-reaction cascade leading to the release of more than one drug-component in sequence with the generation of a fluorescent side product for easy monitoring. As a proof of conc
Stereoselective Synthesis of Coreoside D and Determination of Its Absolute Configuration
Imaizumi, Ryoya,Ogawa, Narihito
supporting information, p. 1409 - 1412 (2020/11/23)
We report the stereoselective synthesis of (3 S)- and (3 R)-coreoside D. The conjugated diyne in the C1-C14 moiety was synthesized through two types of palladium-catalyzed cross-coupling reaction. The introduction of the glucopyranose was achieved by a gl
Diboration of 3-substituted propargylic alcohols using a bimetallic catalyst system: access to (Z)-allyl, vinyldiboronates
Peck, Cheryl L.,Nekvinda, Jan,Santos, Webster L.
supporting information, p. 10313 - 10316 (2020/09/16)
The diboration of substituted propargylic alcohols has been achieved using a bimetallic Pd/Cu catalyst system. Thein situformation of a pentrafluoroboronic acid intermediate sufficiently activates the C-O bond towards dual catalysis affording (Z)-allyl, vinyldiboronates stereoselectively.
Second-Generation Synthesis of the Northern Fragment of Mandelalide A: Role of π-Stacking on Sharpless Dihydroxylation of cis-Enynes
Ghosh, Ankan,Brueckner, Alexander C.,Cheong, Paul Ha-Yeon,Carter, Rich G.
, p. 9196 - 9214 (2019/08/12)
The development of a π-stacking-based approach for increased stereoselectivity in Sharpless asymmetric and diastereomeric dihydroxylation of cis-enynes is disclosed. The use of neighboring, electron-rich benzoate esters proved key to the success of this process. Density functional theory study suggests that the substrate benzoate ester group rigidifies the dihydroxylation transition states by forming a favorable π-stacking interaction in both Major-TS and Minor-TS. The energetic preference for the Major-TS was found in part because of the favorable eclipsing conformation of the alkene substituent as opposed to the disfavored bisecting conformation found in the Minor-TS. The application to a second-generation synthesis of the C15-C24 northern portion of mandelalide A is demonstrated.
Improved synthesis of 2,4,6-trialkylpyridines from 1,5-diketoalkanes: The total synthesis of Anibamine
Miyakoshi, Takeru,Konno, Hiroyuki
, p. 2896 - 2905 (2019/03/21)
Many pyridine syntheses have been developed to date. In this study, we focused on pyridine synthesis with 1,5-diketone derivatives and hydroxylamine. Treatment of simple 1,5-diketoalkanes and hydroxylamine in basic or acidic conditions gave aldol adducts without any pyridine compounds. However, by screening the reaction conditions, we found that acidic conditions produced via the formation of oxime intermediates derived from 1,5-diketoalkanes allowed the formation of the corresponding pyridine derivatives. This is the first example of 2,4,6-trialkylpyridine synthesis from quite simple 1,5-diketoalkanes. In order to demonstrate the utility of the reaction, we demonstrated the synthesis of pyridine derivatives and the total synthesis of a 6-substituted pyridyl-natural product, anibamine. This was achieved by following the above methodology using a reported compound as the starting material to give the product in 12% yield.
Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I
Gangadhar, Pamarthi,Ramakrishna, Sayini,Venkateswarlu, Ponneri,Srihari, Pabbaraja
supporting information, p. 2313 - 2320 (2018/09/14)
The stereoselective total synthesis of strongylodiol H and I has been accomplished. The synthetic procedure comprised the stereoselective reduction of a ketone functionality in an ene–yne–one employing CBS as a catalyst and a Cadiot–Chodkiewicz coupling r
An Atom-Economic and Stereospecific Access to Trisubstituted Olefins through Enyne Cross Metathesis Followed by 1,4-Hydrogenation
Ratsch, Friederike,Schmalz, Hans-Günther
supporting information, p. 785 - 792 (2018/01/27)
The combination of intermolecular enyne cross metathesis and subsequent 1,4-hydrogenation opens a stereocontrolled and atom-economic access to trisubstituted olefins. By investigating different combinations of functionalized alkyne and alkene substrates, we found that the outcome (yield, E / Z ratio) of the Grubbs II-catalyzed enyne cross-metathesis step depends on the substrate's structure, the amount of the alkene (used in excess), and the (optional) presence of ethylene. In any case, the 1,4-hydrogenation, catalyzed by 1,2-dimethoxybenzene-Cr(CO) 3, proceeds stereospecifically to yield exclusively the E -products from both the E- and Z- 1,3-diene intermediates obtained by metathesis. A rather broad scope and functional group compatibility of the method is demonstrated by means of 15 examples.
A remarkably useful sulfur bridge as synthetic lever in an approach to Javanicin B
Dion, Amélie,Spino, Claude
, p. 894 - 919 (2017/07/27)
A concise and efficient synthesis of a non-racemic advanced intermediate to the quassinoid javanicin B is disclosed. The strategy is centred on a triple diene-transmissive Diels-Alder cycloaddition to form the four rings of javanicin B. A sulfur bridge plays several crucial roles allowing an intramolecular cycloaddition to occur with complete stereoselectivity, controlling the stereochemical outcome of another cycloaddition, and transforming into a pivotal electrophile for the introduction of a particularly hindered methyl group.
Activity-Based Probes for 15-Lipoxygenase-1
Eleftheriadis, Nikolaos,Thee, Stephanie A.,Zwinderman, Martijn R. H.,Leus, Niek G. J.,Dekker, Frank J.
supporting information, p. 12300 - 12305 (2016/10/13)
Human 15-lipoxygenase-1 (15-LOX-1) plays an important role in several inflammatory lung diseases, such as asthma, COPD, and chronic bronchitis, as well as various CNS diseases, such as Alzheimer's disease, Parkinson's disease, and stroke. Activity-based probes of 15-LOX-1 are required to explore the role of this enzyme further and to enable drug discovery. In this study, we developed a 15-LOX-1 activity-based probe for the efficient activity-based labeling of recombinant 15-LOX-1. 15-LOX-1-dependent labeling in cell lysates and tissue samples was also possible. To mimic the natural substrate of the enzyme, we designed activity-based probes that covalently bind to the active enzyme and include a terminal alkene as a chemical reporter for the bioorthogonal linkage of a detectable functionality through an oxidative Heck reaction. The activity-based labeling of 15-LOX-1 should enable the investigation and identification of this enzyme in complex biological samples, thus opening up completely new opportunities for drug discovery.
Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines
Zheng, Nan,Chang, Yuan-Yuan,Zhang, Li-Jie,Gong, Jian-Xian,Yang, Zhen
supporting information, p. 371 - 375 (2016/05/19)
A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.
