193416-58-9Relevant academic research and scientific papers
IMMUNOMODULATORY GLYCOSPHINGOLIPIDS AND METHODS OF USE THEREOF
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Page/Page column 41; 43, (2020/08/28)
Provided herein are a subset of alpha-galactosylceramide (alpha-GC) compounds having improved immunomodulatory activity, particularly with respect to NKT cell number and activity. Also provided herein are methods of use of such compounds, including in the modulation of NKT cells and/or activity in vivo. Further provided are combinatorial synthesis methods for generating alpha-GC compounds of specifically defined structure and thereby generating pure preparations thereof.
Stereocontrolled Total Synthesis of Nonenolide
Sudina, Purushotham Reddy,Motati, Damoder Reddy,Seema, Aravind
, p. 1399 - 1404 (2018/06/29)
Nonenolide (1) was first isolated from the entomopathogenic fungus Cordyceps militaries BCC2816 and exhibited good antimalarial activity against Plasmodium falciparum K1. Structurally, it features a decanolide with a trans-double bond attached to two chir
Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks
Show, Krishanu,Kumar, Pradeep
, p. 4696 - 4710 (2016/09/28)
An organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.
Diastereoselective synthesis of the C14-C29 fragment of amphidinol 3
Rival, Nicolas,Hanquet, Gilles,Bensoussan, Charlelie,Reymond, Sebastien,Cossy, Janine,Colobert, Francoise
, p. 6829 - 6840 (2013/10/01)
An efficient stereoselective synthesis of the C14-C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, l-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present in the C14-C29 fragment of amphidinol 3.
Total synthesis and revision of the absolute configuration of seimatopolide B
Reddy, Chada Raji,Dilipkumar, Uredi,Reddy, Motatipally Damoder,Rao, Nagavaram Narsimha
, p. 3355 - 3364 (2013/06/05)
The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxyl
Total synthesis and configurational assignment of the marine natural product haliclamide
Pfeiffer, Bernhard,Speck-Gisler, Sandra,Barandun, Luzi,Senft, Ursula,De Groot, Claire,Lehmann, Irene,Ganci, Walter,Gertsch, Juerg,Altmann, Karl-Heinz
, p. 2553 - 2563 (2013/05/22)
The marine natural product haliclamide has been synthesized based on macrocyclization by ring-closing olefin metathesis. Using either enantiomer of two of the four building blocks that were employed to assemble the diene precursor for the metathesis reaction, three non-natural isomers of haliclamide were also prepared. On the basis of the comparison of the 1H and 13C NMR spectra of the individual stereoisomers with literature data for the natural product, the configuration of the previously unassigned stereocenters at C9 and C20 of haliclamide could be determined to be S for both carbons. The absolute configuration of haliclamide thus is 2S, 9S, 14R, 20S. The antiproliferative activity of synthetic haliclamide against several human cancer cell lines was found to be in the high μM range. The compound showed no antifungal or antibiotic activity.
Total synthesis of phorboxazole A via de novo oxazole formation: Strategy and component assembly
Wang, Bo,Hansen, T. Matthew,Wang, Ting,Wu, Dimao,Weyer, Lynn,Ying, Lu,Engler, Mary M.,Sanville, Melissa,Leitheiser, Christopher,Christmann, Mathias,Lu, Yingtao,Chen, Jiehao,Zunker, Nicholas,Cink, Russell D.,Ahmed, Feryan,Lee, Chi-Sing,Forsyth, Craig J.
scheme or table, p. 1484 - 1505 (2011/04/16)
The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the sequential or simultaneous formation of both of the natural product's oxazole moieties from two serine-derived amides, involving oxidation-cyclodehydrations. The optimized preparation of three pre-assembled components, representing carbons 3-17, 18-30, and 31-46, has been developed. This article details the design and syntheses of these three essential building blocks. The convergent coupling approach is designed to facilitate the incorporation of structural changes within each component to generate unnatural analogues, targeting those with enhanced therapeutic potential and efficacy.
Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive
Mori, Kenji,Shikichi, Yasumasa,Shankar, Shruti,Yew, Joanne Y.
experimental part, p. 7161 - 7168 (2010/10/01)
The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active.
Synthesis of (-)-galantinic acid via iterative hydrolytic kinetic resolution and tethered aminohydroxylation
Dubey, Abhishek,Kauloorkar, Shruti V.,Kumar, Pradeep
experimental part, p. 3159 - 3164 (2010/06/11)
A new synthetic strategy for (-)-galantinic acid is reported using iterative hydrolytic kinetic resolution and tethered aminohydroxylation as the key steps.
Asymmetric total synthesis of rugulactone, an α-pyrone from Cryptocarya rugulosa
Allais, Florent,Aouhansou, Mahoulo,Majira, Amel,Ducrot, Paul-Henri
experimental part, p. 2787 - 2793 (2010/10/18)
A total asymmetric synthesis of rugulactone, a naturally occuring -pyrone isolated from Cryptocarya rugulosa, is reported. The synthesis involved a cross-metathesis coupling reaction to construct the internal E-olefin group, a Still-Gennari olefination to
