51887-25-3Relevant academic research and scientific papers
Asymmetric synthesis of both enantiomers of disparlure
Wang, Zhigang,Zheng, Jianfeng,Huang, Peiqiang
, p. 23 - 28 (2012)
Starting from propargyl alcohol (12), and on the basis of Zhou's modified Sharpless asymmetric epoxidation, the sex pheromone of the Gypsy moth, disparlure (+)-8 and its enantiomer (-)-8 have been synthesized, each in six steps, with overall yields of 29% for (+)-8 and 27% for (-)-8 (ee>98%). The use of the sequential coupling tactic renders the method flexible, which is applicable to the synthesis of other cis-epoxy pheromones. Copyright
CI(NO) Spectra of n-Alkyn-1-ols
Brauner, A.,Budzikiewicz, H.
, p. 324 - 326 (1983)
n-Alkyn-1-ols show fragmentation patterns which are influenced by the length of the chain and by the relative positions of the hydroxyl group and triple bond, and which allow a localization of the site of unsaturation.
Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3-Pyrroline
Cheng, Xinpeng,Zhang, Liming
supporting information, p. 8194 - 8198 (2021/11/01)
This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal-ligand cooperation and the asymmetric induction. 2,5-cis-3-Pyrrolines are formed with excellent diastereoselectivities in a matched scenario. The mismatched scenario by using the ligand enantiomer delivers 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated.
LIPOSOME FORMULATION
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, (2020/12/30)
The present invention describes liposome formulations comprising a phospholipid, cholesterol and a fatty acid compound or fatty acid containing compound. Also, various medical uses of the liposome formulation are described.
Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents
Liu, Lihua,Bao, Xifei,Xiao, Hua,Li, Junlan,Ye, Feifan,Wang, Chaoqin,Cai, Qinhua,Fan, Shilu
, p. 423 - 434 (2019/01/08)
A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.
Synthetic method for American white moth sex pheromone
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Paragraph 0019; 0020; 0022; 0025, (2018/04/01)
The invention provides a synthetic method for an American white moth sex pheromone. 2-propargyl alcohol which is cheap and easy to obtain is used as a raw material, the American white moth sex pheromone a (9S,10R)-9,10-epoxy-(3Z,6Z)-3,6-heneicosadiene is synthesized in a high enantioselectivity and high yield, and enantiomer excess e.e. achieves 99% or more. According to the synthetic method for the American white moth sex pheromone, the production process is safer, the costs are low, the selectivity is higher, and the synthetic method is more energy-saving and environmentally friendly.
Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma
Shimada, Kazuaki,Sugawara, Ayako,Korenaga, Toshinobu,Kawashima, Hideki
, p. 1019 - 1032 (2017/10/07)
In our previous study, unusual odd-numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2?7,18 and 21:2?7,20, through a common pathway involving the strategic combination of alkyne-zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2-propyn-1-ol was at first subjected to alkylation and alkyne-zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C-19 and C-21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z-alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z-alkenyl group. Total synthesis of target fatty acids, 19:2?7,18 and 21:2?7,20, was finally accomplished by two-step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC–MS spectra of the methyl esters of authentic and synthetic fatty acids.
Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization
Ganss, Stephanie,Breit, Bernhard
supporting information, p. 9738 - 9742 (2016/08/10)
A highly attractive route toward macrolactones, which form the cyclic scaffold of a multitude of diverse natural compounds, is described. Although many chemical approaches to this structural motif have been explored, an asymmetric variant of the cyclization is unprecedented. Herein we present an enantioselective macrolactonization through an intramolecular atom-economical rhodium-catalyzed coupling of ω-allenyl-substituted carboxylic acids. The use of a modified diop ligand, chiral DTBM-diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β-unsaturated carboxylic acids and depsipeptides, and provided the desired macrocycles with very high enantio- and diastereoselectivity.
Total synthesis and reassignment of the structures of the antimicrobial lipodepsipeptides circulocin γ and δ
Cochrane, James R.,Exner, Claudia J.,Jolliffe, Katrina A.
, p. 4491 - 4500 (2015/05/13)
The structures of the naturally occurring antimicrobial lipodepsipeptides circulocin γ and circulocin δ have been reported to comprise a common cyclic depsipeptide core attached to 3-hydroxy,ω-guanidino fatty acid chains differing in length by two methyle
Straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain
Romuald, Camille,Cazals, Guillaume,Enjalbal, Christine,Coutrot, Frédéric
supporting information, p. 184 - 187 (2013/03/28)
The straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain, using the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition, is described. The preparation of the nonsymmetrical alkyne azide [c2]daisy chain precursor was realized in situ via the exchange of the monomers contained in both symmetrical alkyne and azide [c2]daisy chains and was followed by mass spectrometry.
