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【期刊论文】Total Synthesis and Structure Revision of Stachybotrys Spirolactams
邓卫平, Wei-Ping Deng, Min Zhong, Xiao-Chuan Guo, and Andrew S. Kende*
J. Org. Chem. 2003, 68, 7422-7427,-0001,():
-1年11月30日
The spirolactam structure 1 reported in 1996 by Roggo et al. has been enantioselectively synthesized in 20 steps from (+)-Wieland-Miescher ketone. Spectra of this synthetic lactam differed from those of the natural spirolactam from the Roggo group, leading to the hypothesis that the natural lactammay be the regioisomer 27, a structure previously ascribed by Jarvis et al. to the natural product stachybotrylactam. This hypothesis was confirmed by the first total synthesis of (-)-stachybotrylactam (27). Double reductive amination of two molecules of aldehyde 29 with one molecule of L-lysine led by analogous chemistry to the first synthesis of the pseudosymmetric "dimer" 30, whose spectra corresponded to those of the natural "dimer" originally assigned structure 5 by the Roggo group.
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【期刊论文】Syntheses of side-chain fluorinated biologically important imidazoles and indoles
邓卫平, Bohumil Dolensky, Ghilsoo Nam, Wei-Ping Deng, Jayan Narayanan, Junfa Fan, Kenneth L. Kirk*
Journal of Fluorine Chemistry 125(2004)501-508,-0001,():
-1年11月30日
We review in this report the preparation of several side-chain fluorinated analogues of biologically important imidazoles and indoles. The building blocks used should also have applications in other synthetic problems. The addition of "FBr" to vinyl imidazole derivatives was used to prepare b-fluoro- and b,b-difluorohistamine and histidinols, as well as b-fluorourocanic acid. Deoxyfluorination of intermediate acylindoles was used to prepare a series of b,b-difluorotryptamine derivative, including the fluorinated analogue of the important neurotransmitter, serotonin.
Imidazoles, Indoles, Biogenic amines, ", FBr", addition, Deoxyfluorination
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