69833-11-0Relevant articles and documents
Exploratory studies towards a synthesis of bioactive kinamycin natural products
Modugu, Nagi Reddy,Vannada, Jagadeshwar,Mehta, Goverdhan
, p. 6919 - 6922 (2015/11/27)
A synthetic approach towards kinamycins that harnesses the proclivities of the norbornyl scaffold is unveiled to access the oxy-functionalized and actively side-armed cyclohexenoid ring-D of these bioactive natural products. This ring-D building block has been further elaborated to the tricyclic ABD ring system present in kinamycins.
Prekinamycin and an isosteric-isoelectronic analogue exhibit comparable cytotoxicity towards K562 human leukemia cells
Abbott, Glenn L.,Wu, Xing,Zhao, Zhufeng,Guo, Lei,Birman, Vladimir B.,Hasinoff, Brian B.,Dmitrienko, Gary I.
, p. 1364 - 1370 (2014/10/15)
The synthesis of N-cyanobenzo[b]carbazoloquinone 4, an isosteric- isoelectronic analogue of prekinamycin, is described. Cytotoxicity studies with K562 human leukemia cells reveal that the cyanamide analogue has a bioactivity profile similar to that of pre
Carbene Ligands as Anthracyclinone Synthons, 6. - Metal Carbene Chelates as Key Reagents in Syntheses of the Daunomycinone Series: Regiospecific Annulation of Arylcarbene Ligands as a Strategy towards the Synthesis of Rings B and C
Doetz, Karl Heinz,Popall, Michael
, p. 665 - 672 (2007/10/02)
Reaction of tetracarbonyl carbene chelates of chromium 4, 5, and 18 with terminal alkynes leads to regiospecific annulation of the carbene ligands to give key intermediates in anthracyclinone synthesis.The B-ring of daunomycinone is formed by reaction of 3-(methoxycarbonyl)-5-hexynoate 1 with the naphthylcarbene complexes 4/5.The metal is recycled as hexacarbonylchromium by decomplexation of the anthracenol complexes 6/7 under CO pressure.Conventional steps lead to the tetracyclic systems 14/15 which serve as precursors to daunomycinone C and its 4-demethoxy analogue.The synthesis of ring C involves the annulation of the anisyl complex 18 by the propargylcyclohexanediones 16/17, and - after cleavage of the metal - leads to the naphthol derivatives 21/22.The functionalization of the ketone 23 to give the acid 24 via isocyanomethyl p-tolyl sulfone and the cyclization using TFA/TFAA are key steps towards the tetracyclic diketone 25 which is a well-known precursor of 11-deoxydaunomycinone E.