18202-10-3Relevant articles and documents
Synthesis and biological evaluation of a "natural" insect repellent
Csuk, René,Niesen, Anja
, p. 934 - 942 (2004)
(11Z)-11,19-Icosadienyl acetate (1) has been shown to be an efficient repellent against the ant Myrmica rubra whereas its corresponding (11E) stereoisomer 2 does not exhibit any repellent activity at all. Several synthetic strategies for these two compounds have been evaluated.
Catalytic asymmetric synthesis of (S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol, an antitumor marine natural product
Liu, Fei-Peng,Zhong, Jiang-Chun,Zheng, Bing,Li, Shuo-Ning,Gao, Gui,Wang, Zhong-Yu,Li, Min-Yan,Hou, Shi-Cong,Wang, Min,Bian, Qing-Hua
, p. 961 - 965 (2015)
Abstract An efficient enantioselective total synthesis of an antitumor marine natural product (S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol 1 with 96% ee and 15% overall yield has been achieved; this is the first preparation of 1 via asymmetric catalytic strategy
Patterned monolayer self-assembly programmed by side chain shape: Four-component gratings
Xue, Yi,Zimmt, Matthew B.
, p. 4513 - 4516 (2012)
A molecular recognition strategy based on alkadiyne side chain shape is used to self-assemble a four-component, 1D-patterned monolayer at the solution-HOPG interface. The designed monolayer unit cell contains six molecules and spans 23 nm × 1 nm. The unit cell's internal structure and packing are driven by complementary shapes and lengths of six different alkadiyne side chains. A solution of the four compounds on HOPG self-assembles monolayers (i) comprised, almost entirely, of the intended unit cell, (ii) exhibiting patterned domains spanning 104 nm2, and (iii) which are sufficiently robust that patterned domains survive solvent rinsing and drying. The patterned monolayer affords 1D-feature spacings ranging from 3.3 to 23 nm. The results demonstrate the remarkable selectivity afforded by molecular recognition based on alkadiyne side chain shape and the ability to program highly complex 1D-patterns in self-assembled monolayers.
Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B
Kirkham, James E. D.,Courtney, Timothy D. L.,Lee, Victor,Baldwin, Jack E.
, p. 5645 - 5647 (2004)
The asymmetric synthesis of the marine sponge natural products, R-strongylodiols A 1 and B 2 using a minimum protection strategy is described. The chirality of the natural products was introduced via the Noyori asymmetric reduction of ynones.
Moth responses to selectively fluorinated sex pheromone analogs
Klun,Schwarz,Wakabayashi,Waters
, p. 2705 - 2719 (1994)
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Total Syntheses of (R)-Strongylodiols C and D
Liu, Feipeng,Zhong, Jiangchun,Li, Shuoning,Li, Minyan,Wu, Lin,Wang, Qian,Mao, Jianyou,Liu, Shikuo,Zheng, Bing,Wang, Min,Bian, Qinghua
supporting information, p. 244 - 247 (2016/02/05)
The first total syntheses of two marine natural products, (R)-strongylodiols C and D, with 99% ee were achieved. The key steps of the strategy include the zipper reaction of an alkyne, the asymmetric alkynylation of an unsaturated aliphatic aldehyde catalyzed with Trost's ProPhenol ligand, and the Cadiot-Chodkiewicz cross-coupling reaction of a chiral propargylic alcohol with a bromoalkyne.
5′-Methylene-triazole-substituted-aminoribosyl uridines as MraY inhibitors: synthesis, biological evaluation and molecular modeling
Fer, Micka?l J.,Bouhss, Ahmed,Patr?o, Mariana,Le Corre, Laurent,Pietrancosta, Nicolas,Amoroso, Ana,Joris, Bernard,Mengin-Lecreulx, Dominique,Calvet-Vitale, Sandrine,Gravier-Pelletier, Christine
, p. 7193 - 7222 (2015/07/01)
The straightforward synthesis of 5′-methylene-[1,4]-triazole-substituted aminoribosyl uridines is described. Two families of compounds were synthesized from a unique epoxide which was regioselectively opened by acetylide ions (for compounds II) or azide ions (for compounds III). Sequential diastereoselective glycosylation with a ribosyl fluoride derivative, Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) with various complementary azide and alkyne partners afforded the targeted compounds after final deprotection. The biological activity of the 16 resulting compounds together with that of 14 previously reported compounds I, lacking the 5′ methylene group, was evaluated on the MraY transferase activity. Out of the 30 tested compounds, 18 compounds revealed MraY inhibition with IC50 ranging from 15 to 150 μM. A molecular modeling study was performed to rationalize the observed structure-activity relationships (SAR), which allowed us to correlate the activity of the most potent compounds with an interaction involving Leu191 of MraYAA. The antibacterial activity was also evaluated and seven compounds exhibited a good activity against Gram-positive bacterial pathogens with MIC ranging from 8 to 32 μg mL-1, including the methicillin resistant Staphylococcus aureus (MRSA).
