87696-33-1Relevant academic research and scientific papers
MEAYAMYCIN ANALOGUES AND METHODS OF USE
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, (2021/10/15)
Compounds according to formula (I), where R is as defined herein, have anti-cancer properties.
Ambruticins: tetrahydropyran ring formation and total synthesis
Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.
, p. 6210 - 6215 (2021/07/28)
The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.
Antifungal water-soluble compound as well as preparation method and application thereof (by machine translation)
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, (2020/06/02)
The invention provides an antifungal water-soluble compound, a preparation method thereof and application, of the compound as I shown in formula. The compound has good antifungal effect and water solubility, can be used for treating and preventing,configuration optical isomers of the optical isomer SRSS obtained by chiral synthesis. (by machine translation)
Total Synthesis of Meayamycin and O-Acyl Analogues
Boger, Dale L.,Chanda, Prem B.,Chowdari, Naidu S.,Gangwar, Sanjeev,Gartshore, Christopher,Momirov, Jelena,Sarkar, Anindya,Tadano, Shinji,Vite, Gregory D.,Zhang, Qian
, (2020/11/18)
A short, scalable total synthesis of meayamycin is described by an approach that entails a longest linear sequence of 12 steps (22 steps overall) from commercially available chiral pool materials (ethyl l-lactate, BocNH-Thr-OH, and d-ribose) and introduces the most straightforward preparation of the right-hand subunit detailed to date. The use of the approach in the divergent synthesis of a representative series of O-acyl analogues is exemplified.
Stereoselective Total Synthesis of Macrophage-Produced Prohealing 14,21-Dihydroxy Docosahexaenoic Acids
Nishimura, Keita,Sakaguchi, Tsuyoshi,Nanba, Yutaro,Suganuma, Yuta,Morita, Masao,Hong, Song,Lu, Yan,Jun, Bokkyoo,Bazan, Nicolas G.,Arita, Makoto,Kobayashi, Yuichi
, p. 154 - 166 (2018/02/19)
Synthesis of 14S,21R- and 14S,21S-dihydroxy-DHA (diHDHA) among the four possible stereoisomers of 14,21-diHDHA was studied. Methyl (R)-lactate (>97% ee), selected as a C20-C22 fragment (DHA numbering), was converted to the C17-C22 phosphonium salt, which was subjected to a Wittig reaction with racemic C16-aldehyde of the C12-C16 part with the TMS and TBS-oxy groups at C12 and C14, yielding the C12-C22 derivative with 14R/S and 21R chirality. Kinetic resolution using Sharpless asymmetric epoxidation of the TBS-deprotected allylic alcohol with l-(+)-DIPT/Ti(O-i-Pr)4 afforded 14S-epoxy alcohol and 14R-allylic alcohol with >99% diastereomeric excess (de) for both. The CN group was introduced to the epoxy alcohol by reaction with Et2AlCN. The 14R-allylic alcohol was also converted to the nitrile via Mitsunobu inversion. Reduction of the nitrile with DIBAL afforded the key aldehyde corresponding to the C11-C22 moiety. The Wittig reaction of this aldehyde with a phosphonium salt of the remaining C1-C10 part followed by functional group manipulation gave 14S,21R-diHDHA. Similarly, ethyl (S)-lactate (>99% ee) was converted to 14S,21S-diHDHA. The chiral LC-UV-MS/MS analysis demonstrated that each of these two 14,21-diHDHAs synthesized using the presented total organic synthesis was highly stereoselective and identical to the macrophage-produced counterpart.
An Olefin Cross-Metathesis Approach to Depudecin and Stereoisomeric Analogues
Cheng-Sánchez, Iván,García-Ruiz, Cristina,Guerrero-Vásquez, Guillermo A.,Sarabia, Francisco
, p. 4744 - 4757 (2017/05/12)
A new total synthesis of the natural product (?)-depudecin, a unique and unexplored histone deacetylase (HDAC) inhibitor, is reported. A key feature of the synthesis is the utilization of an olefin cross-metathesis strategy, which provides for an efficient and improved access to natural depudecin, compared with our previous linear synthesis. Featured by its brevity and convergency, our developed synthetic strategy was applied to the preparation of the 10-epi derivative and the enantiomer of depudecin, which represent interesting stereoisomeric analogues for structure-activity relationship studies.
Further insights into the organocatalytic reaction of 2,2-dimethyl-1,3-dioxan-5-one with α-silyloxy aldehydes
Sánchez, Dani,Carneros, Héctor,Castro-Alvarez, Alejandro,Llàcer, Enric,Planas, Ferran,Vilarrasa, Jaume
, p. 5254 - 5258 (2016/11/11)
Proline-catalysed reactions of dihydroxyacetone isopropylidene acetal, 1, with enantiopure α-silyloxy aldehydes 2/4/6/8 afford 90–95% yields of cross-aldol products (only one stereoisomer in each case), provided that 15 ± 10 equiv of H2O are pr
An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations
Richmond, Edward,Ling, Kenneth B.,Duguet, Nicolas,Manton, Lois B.,elebi-?lcüm, Nihan,Lam, Yu-Hong,Alsancak, Sezen,Slawin, Alexandra M. Z.,Houk,Smith, Andrew D.
, p. 1807 - 1817 (2015/02/19)
The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
A short and facile stereoselective total synthesis of cryptocarya diacetate
Yadav, Jhillu S.,Reddy, P. Murali Krishna,Gupta, Manoj K.,Reddy, Basi V. Subba
, p. 1583 - 1587 (2013/10/22)
A short, simple, and efficient stereoselective total synthesis of cryptocarya diacetate using benzylidene acetal as a key intermediate is described. The synthesis proceeded with overall yield of 10 % starting from commercially available (S)-ethyl lactate.
Synthesis of manzacidin A and C: Efficient construction of quaternary carbon stereocenters bearing nitrogen substituents
Ichikawa, Yoshiyasu,Okumura, Ken,Matsuda, Yasunori,Hasegawa, Tomoyuki,Nakamura, Mitsuhiro,Fujimoto, Aya,Masuda, Toshiya,Nakano, Keiji,Kotsuki, Hiyoshizo
, p. 614 - 622 (2012/02/05)
An efficient synthetic method for stereoselective construction of asymmetric quaternary carbon stereocenters, bearing nitrogen in the form of Boc-protected allyl amines, has been developed. This methodology is employed in the synthesis of marine alkaloids
