92511-96-1Relevant academic research and scientific papers
Addition of silyloxydienes to 2,6-dibromo-1,4-benzoquinone: An approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone
Barker, David,Brimble, Margaret A.,Do, Peter,Turner, Peter
, p. 2441 - 2449 (2007/10/03)
The synthesis of tetraoxygenated bromonaphthoquinones 6a, 6b, 6c, 6d, key intermediates for a synthesis of the 3C protease inhibitor, thysanone, were investigated. Addition of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene 8 to 2,6-dibromo-1,4-benzoquinone 10 in benzene afforded a mixture of naphthoquinone 6a, arising from Diels-Alder addition followed by aromatisation, and Michael adduct 12. The Michael adduct 12 predominated when THF was used as solvent whereas 6a predominated when benzene was used. Naphthoquinone 6a underwent benzylation to naphthoquinone 6c. Addition of 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene 9 to 2,6-dibromo-1,4-benzoquinone 10 followed by benzylation failed to afford the desired bromonaphthoquinone 6d yet methylation did afford naphthoquinone 6b. Bromonaphthoquinone 6d was finally prepared from naphthol 18, obtained from addition of diene 9 to 1,4-benzoquinone 17, followed by ortho-bromination and oxidation. Attempted Sakurai allylation of bromonaphthoquinone 6d afforded naphthodihydrofuran 21. A similar observation was observed for 2-carbomethoxy-1,4-naphthoquinone 22 that also underwent Sakurai allylation to afford naphthodihydrofuran 23. The structure of Michael adduct 12 was confirmed by X-ray crystallography.
Synthesis and Acetylation of Naphthols as Precursors to Naturally Derived Naphthoquinones; Crystal Structure of the Aphin-related 7-O-Methyl Quinone A
Giles, Robin G. F.,Green, Ivan R.,Niven, Margaret L.,Yorke, Selwyn C.
, p. 2459 - 2468 (2007/10/02)
A route is described to 1,5,7-trialkoxy-4-naphthols.A method has been established to convert these compounds into the corresponding 3-acetyl-4-naphthols, in good yield, with a view to synthesizing naturally derived naphthopyran-5,10-quinones.Boron
Selective Acylation of Oxygenated Naphthalenes
Giles, Robin G. F.,Yorke, Selwyn C.,Green, Ivan R.,Hugo, Victor I.
, p. 554 - 555 (2007/10/02)
The synthesis of 1,4,5,7-tetraoxygenated naphthalenes is described, as well as their selective acylation at either C-3 or C-8 using either trifluoroacetic anhydride or acetic acid and trifluoroacetic anhydride; the potential of these reactions in the synt
