164264-14-6Relevant articles and documents
Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPAutilizing an sp3-sp3 Negishi cross-coupling reaction
Tungen, J.o. Eivind,Aursnes, Marius,Dalli, Jesmond,Arnardottir, Hildur,Serhan, Charles Nicholas,Hansen, Trond Vidar
, p. 14575 - 14578 (2014)
The first total synthesis of the lipid mediator MaR1n-3 DPA (5) has been achieved in 12% overall yield over 11 steps. The stereoselective preparation of 5 was based on a Pd-catalyzed sp3-sp3 Negishi cross-coupling reaction and a stereocontrolled Evans-Nagao acetate aldol reaction. LC-MS/MS results with synthetic material matched the biologically produced 5. This novel lipid mediator displayed potent pro-resolving properties stimulating macrophage efferocytosis of apoptotic neutrophils.
An efficient total synthesis of leukotriene B4
Primdahl, Karoline Gangestad,Tungen, Jorn Eivind,Aursnes, Marius,Hansen, Trond Vidar,Vik, Anders
, p. 5412 - 5417 (2015)
Lipid mediators have attracted great interest from scientists within the chemical, medicinal, and pharmaceutical research community. One such example is leukotriene B4 which has been the subject of many pharmacological studies. Herein, we report a convergent and stereoselective synthesis of this potent lipid mediator in 5% yield over 10 steps in the longest linear sequence from commercial starting materials. The key steps were a stereocontrolled acetate-aldol reaction with Nagao's chiral auxiliary and a Z-selective Boland reduction. All spectroscopic data were in agreement with those previously reported.
Evolution of a Strategy for the Total Synthesis of (+)-Cornexistin
Wildermuth, Raphael E.,Steinborn, Christian,Barber, David M.,Mühlfenzl, Kim S.,Kendlbacher, Mario,Mayer, Peter,Wurst, Klaus,Magauer, Thomas
, p. 12181 - 12189 (2021)
Herein is given a full account of the evolution of the first total synthesis of (+)-cornexistin. Initial efforts were based on masking the reactive maleic anhydride moiety as a 3,4-substituted furan and on forming the nine-membered carbocycle in an intramolecular Conia-ene or Nozaki–Hiyama–Kishi (NHK) reaction. Those strategies suffered from low yields and were jeopardized by a late-stage installation of the Z-alkene, as well as the stereocenters along the eastern periphery. These issues were addressed by employing a chiral-pool strategy that involved construction of the crucial stereocenters at C2, C3 and C8 at an early stage with installation of the maleic anhydride as late as possible. The successful approach featured an intermolecular NHK coupling to install the Z-alkene, a syn-Evans-aldol reaction to forge the stereocenters along the eastern periphery, an intramolecular allylic alkylation to close the nine-membered carbocycle, and a challenging stepwise hydrolysis of a β-keto nitrile to furnish the maleic anhydride.
New naphthoquinone and monoterpenoid from Plumbago zeylanica
Ohira, Susumu,Yokogawa, Yoshiaki,Tsuji, Shinji,Mitsui, Taichi,Fukukawa, Tatsuhiko,Hayashi, Ken-Ichiro,Kuboki, Atsuhito,Matsuura, Nobuyasu,Iinuma, Munekazu,Nozaki, Hiroshi
, p. 6554 - 6556 (2014)
New naphthoquinone 2 and new monoterpenoid 3 were isolated from the stems of Plumbago zeylanica, and their structures were determined on the basis of 2D NMR spectroscopy. Absolute configuration of 3 was established by synthesis of its enantiomer. The new naphthoquinone 2 showed potent inhibitory activity against nuclear factor κB (NF-κB), equivalent to that of parthenolide, a known potent inhibitor of NF-κB.
Stereoselective synthesis of the specialized pro-resolving and anti-inflammatory mediator resolvin E1
Nesman, Jannicke Irina,Tungen, J?rn Eivind,Vik, Anders,Hansen, Trond Vidar
, (2019/12/11)
The n-3 polyunsaturated fatty acids eicosapentaenoic acid, docosahexaenoic acid and n-3 docosapentaenoic acid, act as substrates for the biosynthesis of specialized pro-resolving lipid mediators. Resolvin E1, produced from eicosapentaenoic acid, was the first specialized pro-resolving lipid mediator reported. This oxygenated polyunsaturated fatty acid displays a plethora of interesting biological activities, and has entered initial clinical trial development programs. The Evans-Nagao aldol reaction, a stereoselective alkyne reduction and a Z-selective Wittig reaction, were utilized for the stereocontrolled synthesis of resolvin E1 presented herein. In addition, results from HPLC analysis revealed that the synthetic material matched authentic resolvin E1.
PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF
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Page/Page column 39, (2015/06/25)
The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.
SYNTHETIC PRECURSOR OF EPOTHILONE FOR IMPROVING PRODUCTION OF EPOTHILONE AND METHOD FOR PREPARING EPOTHILONE USING THE SAME
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Paragraph 0071; 0072; 0076, (2016/10/10)
The present invention relates to a compound for increasing production of epothilone in actinomyces, and to a method for producing epothilone with increased yield. The method for producing epothilone of the present invention includes a step of culturing actinomyces in which epothilone-biosynthesizing genes in Sorangium cellulosum including epoD, epoE, epoF, orf6, orf3, and orf14 are introduced in a culture medium. According to the present invention, it is possible to increase the production yield of epothilone in actinomyces, even in actinomyces in which epoA, epoP, epoB, and epoC are not introduced therein.COPYRIGHT KIPO 2016
Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants
Schiess, Raphael,Gertsch, Juerg,Schweizer, W. Bernd,Altmann, Karl-Heinz
supporting information; experimental part, p. 1436 - 1439 (2011/05/13)
A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.
First asymmetric total syntheses of (-)-subincanadines A and B, skeletally rearranged pentacyclic monoterpenoid indole alkaloids in Aspidosperma subincanum
Suzuki, Kenta,Takayama, Hiromitsu
, p. 4605 - 4608 (2007/10/03)
We achieved the first asymmetric total syntheses of novel Aspidosperma indole alkaloids, (-)-subincanadines A and B, which involve an intramolecular diastereoselective Pictet-Spengler cyclization and an intramolecular Nozaki-Hiyama-Kishi reaction as key steps in the total syntheses.
Multi-step application of immobilized reagents and scavengers: A total synthesis of epothilone C
Storer, R. Ian,Takemoto, Toshiyasu,Jackson, Philip S.,Brown, Dearg S.,Baxendale, Ian R.,Ley, Steven V.
, p. 2529 - 2547 (2007/10/03)
The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.
