1606589-75-6Relevant academic research and scientific papers
Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge dysidea avara
Fukui, Yurie,Narita, Koichi,Katoh, Tadashi
, p. 2436 - 2439 (2014/03/21)
Dysidavaronea A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o-vanillin. A highly strained and bridged eight-membered carbocyclic core was established by the C7-C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring. The power of a copper enolate! Dysidavaronea A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest linear sequence of 13 steps from commercially available o-vanillin (see scheme; TBS=tert-butyldimethylsilyl). A highly strained and bridged eight-membered carbocyclic core was established by the C7-C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring. Copyright
