53273-37-3Relevant articles and documents
Probing for the pharmacophore of the cytotoxic neoclerodane salvileucalin B
Heinrich, Nora,Banwell, Martin G.,Willis, Anthony C.,Cade, Ian A.,Capon, Robert J.,Huang, Xiao-Cong
, p. 1679 - 1686 (2012)
The novel [4.3.1]propelladiene 2, which embodies the key structural elements of the pentacyclic core of the cytotoxic neoclerodane salvileucalin B (1), has been prepared using a rhodium-catalysed intramolecular Bchner reaction as the key step. Compound 2 and the readily obtained derivatives 12-17 all proved to be essentially inactive when tested against a panel of four human cancer cell lines. Furthermore, not one of these compounds was a P-gp inhibitor.
Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions
Zhang, Lumin,Si, Xiaojia,Yang, Yangyang,Witzel, Sina,Sekine, Kohei,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 6118 - 6123 (2019/07/03)
[Au2(μ-dppm)2]Cl2-mediated photocatalysis reactions are usually initiated by ultraviolet A (UVA) light; herein, an unreported system using blue light-emitting diodes (LEDs) as excitation light source was found. The red shift of the absorption wavelength originates from the combination of [Au2(μ-dppm)2]Cl2 and ligand (Ph3P or mercaptan). On the basis of this finding, a gold-catalyzed reductive desulfurizing C-C coupling of electrophilic radicals and styrenes mediated by blue LEDs is presented, a coupling which cannot be efficiently accessed by previously reported methods. This mild and highly efficient C-C bond formation strategy uses mercaptans both as electron-deficient alkyl radical precursor as well as the hydrogen source. Two examples of amino acids have also been modified by using this strategy. Moreover, this methodology could be applied in polymer synthesis. Gram-scale synthesis and mechanistic insights into this transformation are also presented.
Multiple Halogenation of Aliphatic C?H Bonds within the Hofmann–L?ffler Manifold
Del Castillo, Estefanía,Martínez, Mario D.,Bosnidou, Alexandra E.,Duhamel, Thomas,O'Broin, Calvin Q.,Zhang, Hongwei,Escudero-Adán, Eduardo C.,Martínez-Belmonte, Marta,Mu?iz, Kilian
, p. 17225 - 17229 (2018/11/10)
An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-L?ffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C?H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.
