168169-11-7Relevant articles and documents
Total Synthesis of Dalesconol A by Pd(0)/Norbornene-Catalyzed Three-Fold Domino Reaction and Pd(II)-Catalyzed Trihydroxylation
Zhao, Ping,Guo, Yun,Luan, Xinjun
supporting information, p. 21270 - 21274 (2021/12/27)
Herein, we describe a concise total synthesis of dalesconol A through a “polycyclization/oxidation” approach. In the polycyclization stage, a Pd(0)/NBE-catalyzed 3-fold domino reaction and a subsequent intramolecular Michael addition have been utilized for the one-step assembly of the heptacyclic molecular skeleton. In the late stage of oxidation state adjustments, a stepwise sequence including site-selective benzylic oxidation, Pd(II)-catalyzed oxime ether directed trihydroxylation, and desaturation has been adopted to introduce the oxygen functionalities and furnish the synthesis of dalesconol A. With the advantage of the late-stage amidation of three C–H bonds in a single step, the amino analogue of dalesconol A has also been obtained with high efficiency.
Synthesis, properties, and two-dimensional adsorption characteristics of 5-amino[6]hexahelicene
Van Der Meijden, Maarten W.,Gelens, Edith,Quirs, Natalia Murillo,Fuhr, Javier D.,Gayone, J. Esteban,Ascolani, Hugo,Wurst, Klaus,Lingenfelder, Magal,Kellogg, Richard M.
, p. 1484 - 1492 (2016/01/25)
A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
Transition state analogue inhibitors of protozoan nucleoside hydrolases
Furneaux, Richard H.,Schramm, Vern L.,Tyler, Peter C.
, p. 2599 - 2606 (2007/10/03)
Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C- bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K(i) values in the range 0.2-22 μM against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd.