COC1C=C2C(CCC(=O)C2(C)C)=CC=1.Br[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[OH:24].[OH:25][C:26]1[CH:27]=[CH:28][C:29]2[C:41](=[O:42])[C:40]3C4C(=CC(C#N)=CC=4)N[C:32]=3[C:31](C)(C)[C:30]=2[CH:47]=1>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[C:40]3[C:41](=[O:42])[C:29]4[C:30]([CH2:31][C:32]=3[O:24][C:18]=2[CH:19]=1)=[CH:47][C:26]([OH:25])=[CH:27][CH:28]=4The compounds described in the following Table 43 were synthesized according to the method shown below. According to the method used for the preparation of Compound Z10, Z11 and Z12, 3-chloro-8-methoxy-6H-benzo[b]naphtho[2,3-d]furan-11-one was prepared from Compound A2 and 2-bromo-5-chlorophenol. Subsequently, demethylation was carried out according to the method that is used for the preparation of Compound A6, and thus 3-chloro-8-hydroxy-6H-benzo[b]naphtho[2,3-d]furan-11-one was obtained. Thereafter, according to Mitsunobu reaction that is used for the preparation of Compound A7-1 or the alkylation method that is used for the preparation of A7-17, a corresponding side chain was introduced and, if necessary, functional group modification such as deprotection, etc. was carried out to prepare the compounds listed below.
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