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Figure 2 | Journal of Biomedical Science

Figure 2

From: A novel hydroxyfuroic acid compound as an insulin receptor activator structure and activity relationship of a prenylindole moiety to insulin receptor activation

Figure 2

Preparation of bisindolylhydroxyfuroic acids. i. a) K, t-BuOH, benzene; b) MeI, N,N-dimethylformamide (DMF), 45% (two steps); ii. DDQ, CH2Cl2/H2O (18/1, v/v); 46%; iii. TsCl, 2-butanone, K2CO3, reflux, 86%; iv. OH-, MeOH, H2O, 95%; v. PdCl2 (PPh3)2 (0.1 eq), Na2CO3 (3.0 eq), DMF, 90°C, 12 h, 66%; vi. ClCO2Me (100 mol %), NEt3 (107 mol %), CH2Cl2 (6 mL/mmol 8), DMAP (12 mol %), 60%; vii. a) oxalyl chloride, DMAP (cat.), r.t.; b) 7-substituted indole 10, Et2AlCl, CHCl3, 51-66%; viii. BCl3, CH2Cl2,0°C - r.t.; 80-85%; ix. 5% NaOH in methanol, reflux, 66-70%.

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