121817-36-5Relevant academic research and scientific papers
Synthesis and fungicidal activity of lansiumamide A and B and their derivatives
Xu, Huiyou,Chen, Ting,Huang, Luanbin,Shen, Qiuju,Lian, Zengwei,Shi, Yan,Ouyang, Ming-An,Song, Liyan
, (2018)
A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (N-methyl-N-cis-styryl-cinnamamide, 2) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS,1H NMR, and13C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of N-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.
Total synthesis of lansiumamides A and B and alatamide
Pasqua, Adele E.,Ferrari, Frank D.,Crawford, James J.,Marquez, Rodolfo
, p. 6042 - 6043 (2014)
The total syntheses of lansiumamide A, lansiumamide B and alatamide have been completed taking advantage of the dihalo-olefination of N-formylimides. The syntheses are convergent, flexible and allow for the generation of analogues not accessible through o
Concise and gram-scale total synthesis of lansiumamides A and B and alatamide
Lin, Ran,Lin, Xi,Su, Qian,Guo, Binbin,Huang, Yanqin,Ouyang, Ming-An,Song, Liyan,Xu, Huiyou
, (2019/11/05)
The total synthesis of potent anti-obesity lansiumamide B was accomplished in four steps using commercially available materials. The synthetic strategy, featured with copper-catalyzed Buchwald coupling, is concise, convergent, practical and can be carried out on a one-gram scale. This approach could give either Z- or E-configured enamide moiety in natural products with absolute stereocontrol and was applied in the total synthesis of natural products.
Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization
Cheung, Chi Wai,Buchwald, Stephen L.
, p. 7526 - 7537 (2012/10/30)
A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.
Synthesis of botryllamides and lansiumamides via ruthenium-catalyzed hydroamidation of alkynes
Goossen, Lukas J.,Blanchot, Mathieu,Arndt, Matthias,Salih, Kifah S. M.
supporting information; experimental part, p. 1685 - 1687 (2010/08/20)
Ruthenium-catalyzed hydroamidations of alkynes allow a concise synthetic entry to both E- and Z-configured enamide natural products. This was demonstrated by the synthesis of botryllamides C and E, lansiumamides A and B, and lansamide I in 1-3 steps and 57-98% yield from simple, commercially available precursors. Georg Thieme Verlag Stuttgart New York.
Ruthenium-catalyzed addition of primary amides to alkynes: A stereoselective synthesis of secondary enamides
Goossen, Lukas J.,Blanchot, Mathieu,Salih, Kifah S. M.,Goossen, Kaethe
experimental part, p. 2283 - 2288 (2009/12/27)
The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of Z-configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene) ruthenium(II), 1,4-bis(dic
Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts
Bolshan, Yuri,Batey, Robert A.
, p. 2109 - 2112 (2008/12/23)
(Chemical Equation Presented) A new partner: Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides in the presence of a Cu(OAc)2 catalyst and under mild oxidative conditions (see scheme). The air- and water-stable alkenyltrifluoroborate salts offer a convenient alternative to alkenyl halides as cross-coupling partners. A range of amides undergo coupling including cyclic amides, imides, and carbamates as well as benzamides.
Synthesis of enamides from aldehydes and amides
Bayer, Alexander,Maier, Martin E.
, p. 6665 - 6677 (2007/10/03)
A range of double unsaturated amides (15, 19, and 21), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac2O and pyridine affected clean conversion to the corresponding enamides, such as 42, 45, and 47. Alternatively, N,S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less general. Application of these methods led to the natural products lansiumamide-A (30_cis), lansiumamide-I (31) and lansiumamide-B (32).
Stereoselective synthesis of enamides by a Peterson reaction manifold
Fuerstner, Alois,Brehm, Christof,Cancho-Grande, Yolanda
, p. 3955 - 3957 (2007/10/03)
equation presented Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN3, and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimin
