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.
Penta-deuterated acid precursors in the pheromone biosynthesis of the Egyptian armyworm, Spodoptera littoralis
Munoz, Lourdes,Rosell, Gloria,Guerrero, Angel
, p. 493 - 498 (2009)
Synthesis of penta-deuterated intermediate precursors d5(E)-11-14:Acid (7), d5(Z)-11-14:Acid (10) and d514:Acid (12) of the pheromone of the Egyptian armyworm Spodoptera littoralis has been accomplished by a very convenient route starting from the commerc
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
SYNTHESIS OF (Z)-TETRADEC-11-EN-1-OL AND (Z)-HEXADEC-11-EN-1-OL FROM DODECANE-1,12-DIOL
Zakharkin, L. I.,Guseva, V. V.
, p. 733 - 736 (1984)
A method have been developed for obtaining (Z)-tetradec-11-en-1-ol and (Z)-hexadec-11-en-1-ol via dodec-11-yn-1-ol.
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 and an analogue
Kirkham, James E.D.,Courtney, Timothy D.L.,Lee, Victor,Baldwin, Jack E.
, p. 7219 - 7232 (2005)
The asymmetric synthesis of the marine sponge natural products R-strongylodiols A R-1 and B R-2, using a minimum protection strategy, is described. Two approaches were examined and the Noyori asymmetric reduction of ynones was found to be successful for installing the chirality of the natural products. Analogue R-32 was also prepared. In addition, asymmetric alkynylation of aldehydes is briefly reviewed.
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.
Stereospecificity of an enzymatic monoene 1,4-dehydrogenation reaction: Conversion of (Z)-11-tetradecenoic acid into (E,E)-10,12-tetradecadienoic acid
Rodriguez, Sergio,Clapes, Pere,Camps, Francisco,Fabrias, Gemma
, p. 2228 - 2233 (2002)
In this article, we report the first stereochemical study of an enzymatic 1,4-dehydrogenation reaction, namely, the transformation of (Z)-11-tetradecenoic acid into (E,E)-10,12-tetradecadienoic acid, involved in the sex pheromone biosynthesis of the moth
Quantitative Evaluation of the Effect of the Hydrophobicity of the Environment Surrounding Br?nsted Acid Sites on Their Catalytic Activity for the Hydrolysis of Organic Molecules
Miura, Hiroki,Kameyama, Shutaro,Komori, Daiki,Shishido, Tetsuya
, p. 1636 - 1645 (2019/01/21)
Sulfo-functionalized siloxane gels with a variety of surface hydrophobicities were fabricated to elucidate the effect of the environment surrounding the Br?nsted acid site on their catalytic activity for the hydrolysis of organic molecules. A detailed structural analysis of these siloxane gels by elemental analysis, X-ray photoelectron spectroscopy, Fourier-transformed infrared (FT-IR), and 29Si MAS NMR revealed the formation of gel catalysts with a highly condensed siloxane network, which enabled us to quantitatively evaluate the hydrophobicity of the environment surrounding the catalytically active sulfo-functionality. A sulfo group in a highly hydrophobic environment exhibited excellent catalytic turnover frequency for the hydrolysis of acetate esters with a long alkyl chain, whereas not only conventional solid acid catalysts but also liquid acids showed quite low catalytic activity. Detailed kinetic studies corroborated that the adsorption of oleophilic esters at the Br?nsted acid site was facilitated by the surrounding hydrophobic environment, thus significantly promoting hydrolysis under aqueous conditions. Furthermore, sulfo-functionalized siloxane gels with a highly hydrophobic surface showed excellent catalytic activity for the hydrolytic deprotection of silyl ethers.
A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling
Brunner, Andreas,Hintermann, Lukas
, p. 2787 - 2792 (2016/02/27)
Terminal alkynes (RCCH) are homologated by a sequence of ruthenium-catalyzed anti-Markovnikov hydration of alkyne to aldehyde (RCH2CHO), followed by Bestmann-Ohira alkynylation of aldehyde to chain-elongated alkyne (RCH2CCH). Inverting the sequence by starting from aldehyde brings about the reciprocal homologation of aldehydes instead. The use of 13C-labeled Bestmann-Ohira reagent (dimethyl ((1-13C)-1-diazo-2-oxopropyl)phosphonate) for alkynylation provides straightforward access to singly or, through additional homologation, multiply 13C-labeled alkynes. The labeled alkynes serve as synthetic platform for accessing a multitude of specifically 13C-labeled products. Terminal alkynes with one or two 13C-labels in the alkyne unit have been submitted to alkyne-azide click reactions; the copper-catalyzed version (CuAAC) was found to display a regioselectivity of >50 000:1 for the 1,4- over the 1,5-triazine isomer, as shown analytically by 13C NMR spectroscopy.
