69833-11-0Relevant articles and documents
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
supporting information, 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.
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.
supporting information, 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.
