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. 2020 Mar 19;11(5):773–782. doi: 10.1021/acsmedchemlett.9b00619

Scheme 2.

Scheme 2

Reagents and conditions: (i) (3-methoxyphenyl)boronic acid, Cu(OAc)2·H2O, Py, 4 Å MS, dry CH2Cl2, rt; (ii) Pd(PPh3)4, phenylboronic acid, K2CO3 2 M, DME, MW, 100 °C; (iii) BBr3 1 M in CH2Cl2, dry CH2Cl2, 0 °C; (iv) Cyclohexanol, PPh3, DIAD, dry THF, 0 °C to rt, ultrasound; (v) 2 N NaOH, MeOH/THF, rt; (vi) Tyr methyl ester, TBTU, DIPEA, dry DMSO, rt; (vii) 1 N LiOH, dioxane, rt.