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. 2021 Mar 29;118(14):e2100165118. doi: 10.1073/pnas.2100165118

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Copyright © 2021 the Author(s). Published by PNAS.

This open access article is distributed under Creative Commons Attribution-NonCommercial-NoDerivatives License 4.0 (CC BY-NC-ND).

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Scheme 1. — Synthesis of symmetric (fDAE1-4) and asymmetric hexa-carboxylic acids (fDAE5-6) with a maleimide group. Reagents and conditions: (i) Pd(dba)₂, Sphos, K₂CO₃, aqueous (aq.) THF, reflux, 30 min; (ii) CF₃CO₂H/CH₂Cl₂ (1/1, vol/vol), room temperature (r.t.), 1 h; (iii) nBuLi, −90 °C to r.t., 12 h; (iv) 30% aq. H₂O₂, CH₃COOH, reflux, 1 h; (v) I₂/H₅IO₆, concentrated H₂SO₄, 0 °C, 30 min; (vi) BBr₃, DCM, −10 °C to r.t. 24 h; (vii) TEMPO/BAIB, ACN/H₂O (1/1, vol/vol), r.t., 30 min; and (viii) TSTU/DIPEA, r.t., 10 min, then E/DIPEA, r.t., 30 min.