4147-06-2Relevant articles and documents
Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds
Milic, Dragana,Kop, Tatjana,Juranic, Zorica,Gasic, Miroslav J.,Tinant, Bernard,Pocsfalvi, Gabriella,Solaja, Bogdan A.
, p. 922 - 932 (2005)
A simple approach to aromatization of steroidal quinols and epoxyquinols using a catalytic amount of TMSOTf is reported. Beside acetylation of the angular OH, the acid-catalyzed (TfOH) dienone-phenol rearrangement occurred affording "para" products, or in the case of blocked position 4, the acetoxy group 1,2-migration leads to the formation of "meta" products. Using epoxyquinol derivative as a substrate, the acetoxy group elimination was observed, followed by acid-catalyzed epoxy-ring opening and subsequent double bond migration, giving as a final product Δ9,11A-ring aromatized compounds. Synthesis of conduritol-like compounds and structure confirmation by X-ray crystallography of the precursor of steroidal conduritol is also described. In addition, the results of extensive antiproliferative screening against a panel of 60 cancer cell lines are presented.
Ruthenium-catalyzed oxidation of phenols with alkyl hydroperoxides. A novel, facile route to 2-substituted quinones
Murahashi, Shun-Ichi,Naota, Takeshi,Miyaguchi, Noriko,Noda, Shinji
, p. 2509 - 2510 (2007/10/03)
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