218434-90-3Relevant academic research and scientific papers
Synthesis of Optically Active Maresin 2 and Maresin 2 n-3 DPA
Ogawa, Narihito,Amano, Takahito,Kobayashi, Yuichi
supporting information, p. 295 - 298 (2020/11/18)
Maresins are among the most potent antiinflammatory lipid metabolites. We report stereoselective syntheses of maresin 2 and maresin 2 n-3 DPA. The anti -diol was constructed through epoxide ring opening of an optically active β,γ-epoxy aldehyde, synthesized in situ by Swern oxidation of the corresponding alcohol. Finally, the target compounds were synthesized through a Sonogashira coupling of a C9-C22 iodide and methyl (Z)-oct-4-en-7-ynoate or methyl oct-7-ynoate, respectively.
Fluorine in pheromones: Synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics
Zhang, Qingzhi,Teschers, Charlotte S.,Callejo, Ricardo,Yang, Mingyan,Wang, Mingan,Silk, Peter J.,Ryall, Krista,Roscoe, Lucas E.,Cordes, David B.,Slawin, Alexandra M.Z.,O'Hagan, David
supporting information, p. 2917 - 2922 (2019/04/30)
A series of five 12-dodecanolides have been synthesised containing CF2 groups at C5, C6, C7, C8 and in one case, a double substitution at C5 & C8, as a strategy to bias the conformational space accessed by these macrocycles, and to assess if th
Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965
Kobayashi, Yuichi,Yamaguchi, Kai,Morita, Masao
, p. 1826 - 1831 (2018/03/07)
Allylic substitution of secondary γ,γ-disubstituted allylic picolinates with ArMgBr-based copper reagents was applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity (99%). Ozonolysis, addition of c-Hex-MgBr to the resulting aldehyde, and reductive amination with the piperazine derivative afforded LY426965.
Stereoselective Synthesis of the C(1)?–?C(28) Fragment of Amphidinol 3
Yadav, Jhillu S.,Gopalarao, Yerragorla,Chandrakanth, Dandekar,Reddy, Basi V. Subba
, p. 436 - 446 (2016/07/06)
A stereoselective synthesis of the polyol side chain (C(1)?–?C(28)) of amphidinol 3 has been accomplished following Sharpless epoxidation, Crimmins aldol reaction, Jacobsen kinetic resolution, Sharpless asymmetric dihydroxylation, and our own reaction for
Stereodivergent Intramolecular C(sp3)-H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N -Heterotricycles
Lindsay, Vincent N. G.,Viart, Hélène M.-F.,Sarpong, Richmond
supporting information, p. 8368 - 8371 (2015/07/15)
A general approach for the formation of five-membered saturated heterocycles by intramolecular C(sp3)-H functionalization is reported. Using N-sulfonyltriazoles as Rh(II) azavinyl carbene equivalents, a wide variety of stereodefined cis-2,3-dis
Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes
Elbert, Bryony L.,Lim, Diane S. W.,Gudmundsson, Haraldur G.,O'Hanlon, Jack A.,Anderson, Edward A.
supporting information, p. 8594 - 8598 (2014/07/21)
Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
Asymmetric syntheses of all stereoisomers of 3-hydroxyproline; A constituent of several bioactive compounds
Kumar, Togapur Pavan,Chandrasekhar, Srivari
, p. 2889 - 2894 (2012/10/29)
Synthesis of an unusual β-hydroxy-α-amino acid, 3-hydroxyproline, and its derivatives have been achieved enantioselectively by employing Sharpless asymmetric epoxidation and reductive cyclization as the key steps. Georg Thieme Verlag Stuttgart ? New York.
The natural product CCR5 antagonist anibamine and its analogs as anti-prostate cancer agents
Haney, Kendra M.,Zhang, Feng,Arnatt, Christopher K.,Yuan, Yunyun,Li, Guo,Ware, Joy L.,Gewirtz, David A.,Zhang, Yan
supporting information; experimental part, p. 5159 - 5163 (2011/10/08)
Prostate cancer is a leading cause of death among males in the United States. As the chemokine receptor CCR5 is over-expressed in more aggressive forms of prostate cancer, and is also a critical receptor in inflammation, chemokine receptor CCR5 antagonist
Asymmetric total synthesis of pyranicin
Crimmins, Michael T.,Jacobs, Danielle L.
supporting information; experimental part, p. 2695 - 2698 (2009/10/10)
The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chir
Mechanistic analysis of oxidative C-H cleavages using inter- and intramolecular kinetic isotope effects
Jung, Hyung Hoon,Floreancig, Paul E.
experimental part, p. 10830 - 10836 (2010/02/28)
A series of monodeuterated benzylic and allylic ethers were subjected to oxidative carbon-hydrogen bond cleavage to determine the impact of structural variation on intramolecular kinetic isotope effects in DDQ-mediated cyclization reactions. These values
