1268246-96-3Relevant academic research and scientific papers
Rational synthesis for all All-homocalixarenes
Predeus, Alexander V.,Gopalsamuthiram, Vijay,Staples, Richard J.,Wulff, William D.
, p. 911 - 915 (2013)
Have it all: The synthesis of homocalixarenes of all sizes has been demonstrated using the triple annulation of bis(carbene) complexes with diynes (see scheme). This strategy in principle should allow access to all homocalixarenes. The generality of the synthetic approach is also demonstrated by the preparation of a pyrrole-containing calixarene. Copyright
Synthesis of [m.n]cyclophanes: Regiochemistry transfer from vinyl halides to cyclophanes via fischer carbene complexes
Wang, Huan,Predeus, Alexander V.,Wulff, William D.
, p. 8261 - 8267 (2013)
The double benzannulation of bis-carbene complexes of chromium with α,ω-diynes generates [m.n]cyclophanes in which all three rings are generated in a single reaction. This triple annulation process is very flexible allowing for the construction of symmetrical [n.n]cyclophanes and unsymmetrical [m.n]cyclophanes as well as isomers in which the two benzene rings are both meta bridged or both para bridged, and isomers that contain both meta and para bridges. The connectivity patterns of the bridges in the cyclophanes can be controlled by regioselectivity transfer from the bis-vinyl carbene complexes in which the substitution pattern of the vinyl groups in the carbene complexes dictate the connectivity pattern in the [m.n]cyclophanes. This synthesis of [n.n]cyclophanes is quite flexible with regard to ring size and can be used with tether lengths ranging from n=2 to n=16 and thus to ring sizes with up to 40 member rings. The only limitation to regioselectivity transfer from the carbene complexes to the [m.n]cyclophanes was found in the synthesis of para,para-cyclophanes with four carbon tethers for which the loss of fidelity occurred with the unexpected formation of meta,para-cyclophanes. Put a ring on it: Regiospecificity is the key in the control of the connectivity patterns in [m.n]cyclophanes. Bis-carbene complexes react with diynes to generate all three rings of [m.n]cyclophanes in a single reaction. The regiochemistry of the vinyl groups in the carbene complexes sets the stage for the nature of the linkages in the cyclophanes. Copyright
Total synthesis of iso- and bongkrekic acids: Natural antibiotics displaying potent antiapoptotic properties
Francais, Antoine,Leyva-Perez, Antonio,Etxebarria-Jardi, Gorka,Pena, Javier,Ley, Steven V.
supporting information; experimental part, p. 329 - 343 (2011/03/21)
For over five decades, owing to their antiapoptotic activities, bongkrekic and isobongkrekic acids have generated interest from the scientific community. Here, we disclose full details of our investigation into the synthesis of isobongkrekic acid, which culminated in its first preparation and features various palladium-catalysed cross-couplings and Takai olefination reactions. Access to bongkrekic acid is also reported by this route. These syntheses involve the preparation and use of new general building blocks which could find wider applications. Iso-bong: A versatile first synthesis of isobongkrekic acid (IBA) has been developed. Key steps include three different palladium cross-couplings and an asymmetric homopropargylation. In-depth synthetic studies reveal the challenges faced in generating the right geometry of each diene.
