83570-33-6Relevant academic research and scientific papers
Intramolecular Acetalisation of Naphthoquinones
Hudson, Alan T.,Pether, Michael J.,Ferrige, Anthony G.,Lindon, John C.
, p. 1933 - 1936 (2007/10/02)
Attempts have been made to synthesise the glyceride quinone 2-cyclohexyl-3-(1,2-dihydroxyethyl)methoxy-1,4-naphthoquinone (3) as a prodrug of 2-cyclohexyl-3-hydroxy-1,4-naphthoquinone (4).The intermediate 2-cyclohexyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl methoxy)-1,4-naphthoquinone (6), required for the projected synthesis, was readily obtained.However, on acid treatment this compound unexpectedly furnished 5-cyclohexyl-10b,2-epoxymethano- (7) and 5-cyclohexyl-10b,3-epoxymethano-2,3-dihydronaphthodioxin-6(10bH)-one (8).The structures of these compounds have been established by spectroscopic and degradative studies and a mechanism is proposed to account for their formation.
