121817-37-6Relevant academic research and scientific papers
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.
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
, (2018/07/10)
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
supporting information, p. 6042 - 6043 (2015/01/09)
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
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.
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).
Unsaturated enamides via organometallic addition to isocyanates: The synthesis of Lansamide-I, Lansiumamides A-C and SB-204900
Stefanuti, Ian,Smith, Stephen A.,Taylor, Richard J. K.
, p. 3735 - 3738 (2007/10/03)
Styryl Grignard addition to vinyl isocyanates is employed to prepare the naturally occurring enamides Lansamide-I, Lansiumamides A and B, and SB- 204900; the synthesis of Lansiumamide C is also reported. (C) 2000 Elsevier Science Ltd.
