69833-11-0Relevant academic research and scientific papers
Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization
Ando, Yoshio,Hori, Subaru,Fukazawa, Takumi,Ohmori, Ken,Suzuki, Keisuke
, p. 9650 - 9653 (2015/08/11)
A viable method is reported for the synthesis of the bicyclo[3.2.1]octadienone scaffold in naturally occurring octaketide dimers. The procedure employs a reductive cyclization reaction mediated by an unusual ethanedithiol monosodium salt. Doubling up: A viable method for the construction of bicyclo[3.2.1]octadienone scaffolds has been developed, involving the reductive cyclization of dimeric naphthoquinone monoacetal mediated by the monosodium salt of 1,2-ethanedithiol. Bicyclo[3.2.1]octadienones may serve as key core units in the synthesis of biologically relevant naphthocyclinones.
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
Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
Nishino, Hiroshi,Tsunoda, Katsunori,Kurosawa, Kazu
, p. 545 - 550 (2007/10/02)
The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.
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.
