104501-60-2Relevant academic research and scientific papers
Total Synthesis and Structure Revision of Diplobifuranylone B
Cheng, Xinpeng,Quintanilla, Carlos D.,Zhang, Liming
, p. 11054 - 11060 (2019)
An asymmetric total synthesis of diplobifuranylone B was achieved in 10 steps for the longest linear sequence and in 15.8% overall yield from commercially available methyl (R)-(+)-lactate and l-glutamic acid. This synthesis features a stereoselective construction of the key 2,5-dihydrofuran ring in the natural product via a recently developed asymmetric gold catalysis. The stereochemical flexibility offered by the catalysis enables an expedient revision of the reported structure of diplobifuranylone B, where the relative stereochemistry of the 2,5-dihydrofuran moiety was previously misassigned as cis instead of trans.
Studies towards the synthesis of trocheliophorolides
Khomane, Navnath B.,Meshram, Harshadas M.,Rode, Haridas B.
, p. 2157 - 2160 (2018)
Total synthesis of trocheliophorolide C epimer is reported. The synthetic strategy involves generation of lactone skeleton and preparation of unsaturated side chain followed by cross-metathesis. The Eglinton oxidative coupling, Cadiot-Chodkiewicz cross-coupling and cross-metathesis are the key reactions used in the synthesis. We also attempted the synthesis of trocheliophorolide D epimer, which includes Cu catalyzed various cross-coupling reactions.
A modular approach to polyketide building blocks: Cycloadditions of nitrile oxides and homoallylic alcohols
Lohse-Fraefel, Nina,Carreira, Erick M.
, p. 2011 - 2014 (2005)
(Chemical Equation Presented) A general approach to the diastereoselective synthesis of Δ2-isoxazolines via magnesium-mediated, hydroxyl-directed diastereoselective nitrile oxide cycloadditions of homoallylic alcohols and monoprotected homoallylic diols is disclosed. A broad spectrum of aliphatic and aromatic nitrile oxides and a variety of homoallylic alcohols participate in the cycloaddition, thus expanding the scope of polyketide building blocks that can be accessed using this strategy.
REAGENT-CONTROLLED ENANTIOSELECTIVE HOMOALDOL REACTION WITH CHIRAL 1-OXYALLYLLITHIUM DERIVATIVES. ENANTIO-DIVERGENT TUNING BY ACHIRAL TITANIUM REAGENTS
Kraemer, Thomas,Hoppe, Dieter
, p. 5149 - 5152 (1987)
Optically active 2-alkenyl carbamates are deprotonated by n-butyllithium with retention of configuration.Lithium titanium exchange by Ti(OiPr)4 proceeds with retention and by ClTi(NEt2)3 with inversion of configuration.The stereochemical course of addition to aldehydes is mainly determined by the chiral center of the metal allyl reagents to offer a flexible route to both enantiomers of highly substituted ketones.
Stereoselective Access to (E)-1,3-Enynes through Pd/Cu-Catalyzed Alkyne Hydrocarbation of Allenes
Jeanne-Julien, Louis,Masson, Guillaume,Kouoi, Remy,Regazzetti, Anne,Genta-Jouve, Grégory,Gandon, Vincent,Roulland, Emmanuel
, (2019)
PdII and CuI cooperate in catalyzing the alkynes hydrocarbation of allenes (AHA) giving (E)-1,3-enynes with high yields, atom economy, and high regio-/stereoselectivities. We devised new efficient conditions and expanded the substrat
Asymmetric total synthesis of PM-toxin A, a corn host-specific pathotoxin
Hayakawa, Hiroyuki,Ohmori, Makiko,Takamichi, Kiyoko,Matsuda, Fuyuhiko,Miyashita, Masaaki
, p. 1219 - 1220 (1997)
The first asymmetric total synthesis of PM-toxin A, a corn host-specific toxin produced by the fungal pathogen Phyllosticta maydis, starting from D-lactate is described.
Total synthesis of (+)-cephalosporolide E and (-)-cephalosporolide F en route to bassianolone
Fernandes, Rodney A.,Ingle, Arun B.
, p. 158 - 160 (2010)
A stereoselective synthesis of (+)-cephalosporolide E and (-)-cephalosporolide F en route to bassianolone is described. The key steps involve cross metathesis to get the desired β ,γ-unsaturated ester, asymmetric dihydroxylation to install the β-hydroxy-γ-lactone moiety and spiroketalization. Although attempts to get free bassianolone failed, the first total synthesis of natural cephalosporolides E and F has been achieved in nine steps and 6.3% and 3.5% overall yields, respectively. Georg Thieme Verlag Stuttgart.
Structure–activity relationship study of the anti-obesity natural product yoshinone A
Kawazoe, Yoshinori,Itakura, Yuki,Inuzuka, Toshiyasu,Omura, Sachikazu,Uemura, Daisuke
, p. 226 - 232 (2021)
Yoshinone A was derived from marine algae and shown to inhibit adipogenic differentiation. The natural compound is composed of a γ-pyrone ring and a side chain and that contains two asymmetric carbons. Although their absolute configuration has been determ
C11-CYCLIC SUBSTITUTED 13-MEMBERED MACROLIDES AND USES THEREOF
-
, (2020/06/10)
Provided are 13-membered macrolides for the treatment of infectious diseases. The 13- membered macrolides described herein are azaketolides. Also provided are methods for preparing the 13-membered macrolides, pharmaceutical compositions comprising the 13-
Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization
Yalamanchili, Subbarao,Miller, William,Chen, Xizhao,Bennett, Clay S.
supporting information, p. 9646 - 9651 (2019/12/02)
A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-pyran-4-ones in good t
