ISSN:
0170-2041
Keywords:
Hallachrome
;
1,2-Anthraquinones
;
9,10-Anthraquinones
;
Oxygenation
;
1-Anthracenols
;
Mimoun complex
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
9,10-Anthraquinones 3b-3k are prepared by Diels-Alder reaction of juglone (5a) and 7-methyljuglone (5b) with the dienes 4a and 4b, then reduced to the corresponding 1-anthracenols 2b-2d, 2f and 2i that are immediately oxygenated to the ortho-anthraquinones 1b-1d, 1f and 1i with [MoO(O2)2]·py·HMPT. The 1,2-anthraquinones dimerize in solution or upon BBr3 treatment. The naturally occurring 1,2-anthraquinone hallachrome (1a) is prepared by selective protection of the bisphenol 3h as monosilyl ether 3i, oxygenation to the silylated ortho-anthraquinone 1i and fluoride-mediated deprotection to 1a.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301142
Permalink
