Here,we describe a general and modular strategy for the rapid assembly of benzo[c]phenanthridine(BCP)derivatives using homogeneous gold catalysis.Notably,in contrast to traditional methods based on the specially prefo...Here,we describe a general and modular strategy for the rapid assembly of benzo[c]phenanthridine(BCP)derivatives using homogeneous gold catalysis.Notably,in contrast to traditional methods based on the specially preformed substrates that have an inherent preference for the formation of this class of compounds with limited flexibility,this protocol is achieved via a selectively intramolecular cascade of a diazo-tethered alkyne and subsequently an intermolecular cyclization with a nitrile to facilitate the successive C–N and C–C bonds formation.This methodology uses readily available nitriles as the nitrogen source to deliver the products in good yield with excellent functional group compatibility.A preliminary anti-tumor activity study of these generated products exhibits high anticancer potency against five tumor cell lines,including He La,Mel624,SW-480,8505C,LAN-1.Besides,we report a catalyst-controlled intermolecular cycloaddition/intramolecular insertion of the substrate with a fulvene to provide fused polycarbocycles containing a seven-membered ring.展开更多
This review summarizes recent advances in the field of gold-catalyzed synthesis of pharmaceutically relevant aza-heterocycles via in situ generated a-imino gold carbene complexes as intermediates.
A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones,starting from easy to synthesise alkynyl phosphonates,is presented.With the aid of a pyridine-N-oxide,in a goldcatalysed step...A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones,starting from easy to synthesise alkynyl phosphonates,is presented.With the aid of a pyridine-N-oxide,in a goldcatalysed step anα-oxo carbene species is generated as a key intermediate.After formal OH-insertion,synthetically useful HWE reagents can be attained.The synthetic utility of the obtained building blocks could be demonstrated,which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.展开更多
文摘Here,we describe a general and modular strategy for the rapid assembly of benzo[c]phenanthridine(BCP)derivatives using homogeneous gold catalysis.Notably,in contrast to traditional methods based on the specially preformed substrates that have an inherent preference for the formation of this class of compounds with limited flexibility,this protocol is achieved via a selectively intramolecular cascade of a diazo-tethered alkyne and subsequently an intermolecular cyclization with a nitrile to facilitate the successive C–N and C–C bonds formation.This methodology uses readily available nitriles as the nitrogen source to deliver the products in good yield with excellent functional group compatibility.A preliminary anti-tumor activity study of these generated products exhibits high anticancer potency against five tumor cell lines,including He La,Mel624,SW-480,8505C,LAN-1.Besides,we report a catalyst-controlled intermolecular cycloaddition/intramolecular insertion of the substrate with a fulvene to provide fused polycarbocycles containing a seven-membered ring.
基金Zhao X is grateful to the China Scholarship Council for a Ph.D.fellowship。
文摘This review summarizes recent advances in the field of gold-catalyzed synthesis of pharmaceutically relevant aza-heterocycles via in situ generated a-imino gold carbene complexes as intermediates.
基金S.T.acknowledges the financial support by the DAAD PhDprogramJ.F.W.thanks the support from the Hector Fellow AcademyThe authors acknowledge the support by the state of Baden-Württemberg through bwHPC.
文摘A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones,starting from easy to synthesise alkynyl phosphonates,is presented.With the aid of a pyridine-N-oxide,in a goldcatalysed step anα-oxo carbene species is generated as a key intermediate.After formal OH-insertion,synthetically useful HWE reagents can be attained.The synthetic utility of the obtained building blocks could be demonstrated,which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.
