Skip to main content
. Author manuscript; available in PMC: 2020 Mar 30.
Published in final edited form as: ChemistrySelect. 2018 Nov 29;3(44):12625–12629. doi: 10.1002/slct.201802475

Scheme 3. Construction of aromatic fragments.

Scheme 3.

Reagents and conditions: (a) aq. LiOH, THF, 45 °C, 91–95%; (b) TMSEOH (1.2 equiv.), EDCI (1.0 equiv.), NEt3 (2.0 equiv.), DCM, 25 °C, 12 h, 89%; (c) H2 (1.1 atm.), 10% Pd/C (0.2 equiv.), MeOH, 25 °C, 3 h, 95% (for 13), 91% (for 15a), 89% (for 15b), 93% (for 17a), 82% (for 17b), 89% (for 19), 84% (for 21a), 92% (for 21b), 87% (for 24); (d) TMSEOH (1.5 equiv.), toluene, Bu2SnO (1.0 equiv.), 150 °C, 85–95%; (e) AlCl3 (3.0 equiv.), 1,2-DCE, 90 °C, 85%; (f) BnBr, K2CO3, acetone, 3 h, 87%; (g) Bi(NO3)3.5H2O (1.0 equiv.), MMT K10 (1.0 equiv.), DCM, 25 °C, 2 h, 81%. Abbreviations: THF = tetrahydrofuran, TMSE = 2-(trimethylsilyl)ethyl, Bu = butyl, MMT K10 = bentonite clay K-10.