108794-10-1Relevant articles and documents
Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones
Wu, Fu-Peng,Yuan, Yang,Schünemann, Claas,Kamer, Paul C. J.,Wu, Xiao-Feng
, p. 10451 - 10455 (2020)
The borocarbonylative coupling of unactivated alkenes with alkyl halides remains a challenge. In this communication, a Cu-catalyzed borocarbonylative coupling of unactivated alkenes with alkyl halides for the synthesis of β-boryl ketones has been developed. A broad range of β-boryl ketone derivatives was prepared in moderate to excellent yields with complete regioselectivity.
Control of the Regioselectivity in Cobalt- versus Ruthenium-Catalyzed Alder-ene Reaction of Unsymmetrical 1,3-Diynes
Weber, Sebastian M.,Hilt, Gerhard
, p. 564 - 567 (2017)
The Alder-ene reaction of trialkylsilyl-substituted 1,3-butadiynes with terminal alkenes was investigated utilizing a cobalt-based catalyst, and the results were compared with Alder-ene rections catalyzed by the [CpRu(H3CCN)3]PF6 catalyst. Obviously, the two catalysts gave complementary results of yn-dienes differing in the site where the new carbon-carbon bond was formed. Of particular interest are observations concerning the double bond migration within the alkene component. While simple alkenes gave exclusively the E-configuration, the application of 3-buten-1-ol resulted in the corresponding Z-double bond, indicating that the hydroxyl group acts as donor coordinating to the cobalt center and thereby altering the reaction pathway.
A total synthesis of epothilones using solid-supported reagents and scavengers
Storer, R. Ian,Takemoto, Toshiyasu,Jackson, Philip S.,Ley, Steven V.
, p. 2521 - 2525 (2003)
A total synthesis of epothilone C(1) with concomitant formal synthesis of epothilone A is described, using immobilized reagents and scavengers to effect multistep synthetic transformations and purifications.
Highly efficient asymmetric synthesis of fluvirucinine A1 via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-lipase-catalyzed acetylation tandem process
Liang, Bo,Negishi, Ei-Ichi
, p. 193 - 195 (2008)
(Chemical Equation Presented) ZACA-lipase-catalyzed acetylation tandem process has been shown to proceed satisfactorily with either TBS-protected 4-penten-1-ol or 3-buten-1-ol to provide the corresponding enantiomerically pure (R)-2-ethyl-1-alkanols. Either (R)-5 or (R)-6 was converted to 3 in seven steps. The other fragment 4 was synthesized in nine steps from (-)-(S)-citronellol. Conversion of 3 and 4 into 99% pure fluvirucinine A 1 was achieved in four steps via amidation-ring closing metathesis, the overall yield in the longest linear sequence being 34% (13 steps).
Truncated Latrunculins as Actin Inhibitors Targeting Plasmodium falciparum Motility and Host Cell Invasion
Johnson, Swapna,Rahmani, Rapha?l,Drew, Damien R.,Williams, Melanie J.,Wilkinson, Mark,Tan, Yan Hong,Huang, Johnny X.,Tonkin, Christopher J.,Beeson, James G.,Baum, Jake,Smith, Brian J.,Baell, Jonathan B.
, p. 10994 - 11005 (2016)
Polymerization of the cytosolic protein actin is critical to cell movement and host cell invasion by the malaria parasite, Plasmodium falciparum. Any disruption to actin polymerization dynamics will render the parasite incapable of invading a host cell and thereby unable to cause infection. Here, we explore the potential of using truncated latrunculins as potential chemotherapeutics for the treatment of malaria. Exploration of the binding interactions of the natural actin inhibitor latrunculins with actin revealed how a truncated core of the inhibitor could retain its key interaction features with actin. This truncated core was synthesized and subjected to preliminary structure-activity relationship studies to generate a focused set of analogues. Biochemical analyses of these analogues demonstrate their 6-fold increased activity compared with that of latrunculin B against P. falciparum and a 16-fold improved selectivity ex vivo. These data establish the latrunculin core as a potential focus for future structure-based drug design of chemotherapeutics against malaria.
Formal synthesis of dictyostatin and synthesis of two dictyostatin analogues
Gallon, Julien,Esteban, Jorge,Bouzbouz, Samir,Campbell, Matthew,Reymond, Sébastien,Cossy, Janine
, p. 11788 - 11797 (2012)
A formal convergent synthesis of dictyostatin from (R)-Roche ester is described. Synthetic highlights include a Ni-catalyzed Nozaki-Hiyama-Kishi coupling between an aldehyde and a Z vinyl iodide to assemble the two main fragments, a diastereoselective Myers alkylation, a stereoselective Evans aldolization, two asymmetric Duthaler crotyltitanations, and a stereoselective Pd-catalyzed Marshall allenylindium addition to install the stereogenic centers of dictyostatin. The synthesis of (9R)-epi-dictyostatin and a new ring-contracted dictyostatin isomer were also achieved. Copyright
The total synthesis of (-)-aurafuron A
Hartmann, Olaf,Kalesse, Markus
, p. 3064 - 3067 (2012)
The first total synthesis of (-)-aurafuron A is presented. It features a Suzuki cross-coupling reaction and a high yielding anionic aldol addition as central carbon skeleton building reactions. The synthesis confirms the proposed structure including its configuration and allows for detailed SAR studies.
Formal chemoselective synthesis of leucascandrolide A
Ferrie, Laurent,Reymond, Sebastien,Capdevielle, Patrice,Cossy, Janine
, p. 2461 - 2464 (2007)
A chemoselective synthesis of ths macrocyclic cors of leucascandrolide A has been achieved, utilizing highly enantioselective allylmetalations, an enantioselective Noyori reduction of a propargylic ketone and olefin metatheses as the key steps.
Studies on the synthesis of the lasubine alkaloids
Mohamed Aslam, Nur Filza bte,Simon, Oliver,Bates, Roderick W.
, p. 5032 - 5039 (2018)
Formal syntheses of lasubine II and subcosine II have been completed by the synthesis of epi-lasubine II. The synthesis involves diastereoselective allylation of a methoxy isoxazolidine and a tandem hydrogenation process leading stereoselectively to a tri
Fast and efficient synthesis of novel fumagillin analogues
Baldwin, Jack E,Bulger, Paul G,Marquez, Rodolfo
, p. 5441 - 5452 (2002)
A novel class of non-carbocyclic ring analogues of the potent angiogenesis inhibitors fumagillin and TNP-470 have been enantioselectively and efficiently synthesised starting from pyridine-2-thiol in 10 steps in excellent overall yield.
