Retinoids and Related Compounds; 18: A Convenient Synthesis of Retinoic Acid Analogs Having an Anthraquinone Ring

Akimori Wada; Chisato Tode; Saeko Hiraishi; Yukiko Tanaka; Tomoko Ohfusa; Masayoshi Ito

doi:10.1055/s-1995-4063

Synthesis 1995; 1995(9): 1107-1110
DOI: 10.1055/s-1995-4063

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Retinoids and Related Compounds; 18: A Convenient Synthesis of Retinoic Acid Analogs Having an Anthraquinone Ring

Akimori Wada, Chisato Tode, Saeko Hiraishi, Yukiko Tanaka, Tomoko Ohfusa, Masayoshi Ito^*

^*Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658, Japan, Fax +81(78)4417562

Abstract

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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.

retinoic acid - retinoic acid analog - anthraquinone - sulfone compounds - retinoidal activity

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