1614247-91-4Relevant articles and documents
Aromatics to bis-triquinane: A tandem oxidative dearomatization of bis-phenol, cycloaddition, photorearrangement and a rapid entry into carbocyclic framework of Xeromphalinone e
Singh, Deepak,Chaudhari, Umesh V.,Deota, Pradeep T.
, p. 4485 - 4493 (2014/06/10)
A novel approach for the synthesis of a bird-shaped bis-triquinane 3, a fascinating carbocyclic framework closely related to the skeleton of Xeromphalinone E 1 from readily available 2,6-dimethyl phenol 8 has been reported. The synthesis of bis-cyclohexadienones 6, 22a-e by oxidative acetylation of tetramethyl bisphenols 7, 20a-e has been investigated using two different reagents under varying reaction conditions. The cycloaddition of bis-cyclohexadienone 6 gives two carbocycles, bis-adduct 4b and mono-adduct 5d in a stereocontrolled manner. The photochemical sigmatropic 1,2-acyl shift in 4b furnished 3 and monotriquinane 9 linked with a 9-acetoxy-9-methyl-endo- tricyclo[5,2,2,02,6]undeca-4,10-diene-8-one system. Two different pentasubstituted phenols 13 and 14 were also isolated during an attempted oxa-di-π-methane (ODPM) rearrangement of mono-adduct 5d via aromatisation of the cyclohexadienone ring. The photochemical behaviour of bis-cyclohexadienones 6, 22a-e has also been investigated under UV irradiation and two different aromatized products were isolated for each bis-cyclohexadienone by migration and elimination of acetate groups.
