16101-72-7Relevant academic research and scientific papers
Synthesis and biological evaluation of ABCD ring fragments of the kibdelones
Sloman, David L.,Mitasev, Branko,Scully, Stephen S.,Beutler, John A.,Porco Jr., John A.
supporting information; experimental part, p. 2511 - 2515 (2011/05/04)
Arylation goes platinum: The synthesis of the ABCD ring fragments of the kibdelones has been achieved through a novel PtIV-catalyzed arylation of a quinone monoketal followed by photocyclization (see scheme). Biological evaluation in the NCI 60-cell screen revealed that the kibdelone ABCD ring analogues were about 2000 times less active than kibdelones B and C, suggesting that the tetrahydroxanthone structure of the kibdelones is crucial for cytotoxicity. Copyright
A Synthesis of Polycyclic Aromatic Compounds by the Ca(OAc)2-Induced Aromatization of Polyoxoalkanedioates Generated from Diesters and Acetoacetate Dianion
Yamaguchi, Masahiko,Hasebe, Koichi,Higashi, Hirofumi,Uchida, Minoru,Irie, Akemi,Minami, Toru
, p. 1611 - 1623 (2007/10/02)
The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part.The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxyanthracenes.The latters were air-oxidized to anthraquinones in the presence of K2CO3.The regiochemistry of the arene synthesis was studied.As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out.Pentacenequinones were synthesized from anthracenes, while anthraquinones gave naphthacenequinones.The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis.A formal synthesis of aklavinone was achieved.
