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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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邓卫平, Andrew S. Kende, * Wei-Ping Deng, Min Zhong, and Xiao-Chuan Guo
Org. Lett., Vol. 5, No.10, 2003,-0001,():
-1年11月30日
The enantioselective total synthesis and structure revision of spirodihydrobenzofuranlactam 1 and of its regioisomer 25 are presented. Optically pure (+)-Wieland-Miescher ketone was utilized to construct the AB bicyclic core in 10 steps. Introduction of the resorcylate D-ring unit was achieved by use of our tert-butyl ester metalation sequence. Subsequent stereoselective spirocyclization to form the C-ring was followed by regioselective ring cyanation and lactam formation to produce the pentacyclic structure 1 and its regioisomer 25.
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【期刊论文】Convenient syntheses of 2-, 5-and 6-fluoro-and 2,6-difluoro-L-DOPA
邓卫平, Wei-Ping Deng, Kelli A. Wong and Kenneth L. Kirk*
Tetrahedron: Asymmetry 13(2002)1135-1140,-0001,():
-1年11月30日
Alkylation under phase transfer conditions of the chiral glycine synthon 2 (prepared from the commercially available Oppolzer chiral sultam) with fluorinated analogues of 3,4-dimethoxybenzyl chloride proceeded with high diastereoselectivity. Hydrolysis of the Schiff base, removal of the chiral auxiliary and HBr demethylation produced 2-, 5-, 6-fluoro- and 2,6-difluoro-LDOPA in e.e. of >99%.
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邓卫平, Wei-Ping Deng, Xue-Long Hou, * Li-Xin Dai, Yi-Hua Yu and Wei Xia
Chem. Commun., 2000, 285-286,-0001,():
-1年11月30日
A series of planar chiral 1,1A-P,N-2A-substituted ferrocene ligands 9-12 and 16, prepared with diastereopurity > 99+1, have been used to examine the role of planar chirality, and significant effects on enantioselectivity as well as the control of absolute configuration in palladium-catalyzed allylic alkylation as a model reaction were observed.
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邓卫平, Wei-Ping Deng, An-Hu Li, Li-Xin Dai* and Xue-Long Hou
Tetrahedron 56(2000)2967-2974,-0001,():
-1年11月30日
--On treatment of N-tosylimines 1 and 4-hydroxyl-cis-butenyl arsonium salt 5 or sulfonium salt 11a with KOH in acetonitrile at room temperature, 2-(a-substituted N-tosylaminomethyl)-2,5-dihydrofurans 4 were obtained in moderate yields through a new ylide
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