Synthesis p. 1107 - 1110 (1995)
Update date:2022-08-29
Topics:
Wada
Tode
Hiraishi
Tanaka
Ohfusa
Ito
Synthesis of retinoic acid analogs involving an anthraquinone ring is described. The reaction of p-toluenesulfonylmethylanthraquinones 8 with ethyl 8-chloro-3,7-dimethyl-2,4,6-octatrienoate (6) and subsequent desulfonylation afforded the esters 10 and 11 as a mixture of terminal double bond isomers. After separation of these isomers, basic hydrolysis using 10% potassium hydroxide gave the corresponding acids 12 and 13, respectively, without isomerization of the terminal double bond in excellent yields.
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Doi:10.1016/0040-4039(94)02395-R
(1995)Doi:10.1016/j.tet.2015.05.061
(2015)Doi:10.1016/j.tet.2004.06.117
(2004)Doi:10.1016/0040-4020(67)80052-8
(1967)Doi:10.1039/b712901g
(2008)Doi:10.3987/COM-18-13876
(2018)