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. 2021 May 27;64(11):7809–7838. doi: 10.1021/acs.jmedchem.1c00644

Scheme 5. Synthesis of Compounds 68 and 72.

Scheme 5

Reagents and conditions: (i) cyclopentanol, EDC, DMAP, DCM, rt; (ii) 1-octadecanol, pTsOH, toluene, reflux; (iii) TFA/DCM (1:5), rt; (iv) Boc-l-Val, DCC, HOBt, Et3N, DMAP, EtOAc, rt; (v) Boc-l-Val, EDC, HOBt, DIPEA, DMAP, DCM, rt; (vi) Boc-Gly, DCC, HOBt, Et3N, DMAP, EtOAc, rt, or Boc-Gly, EDC, HOBt, DIPEA, DMAP, DCM, rt; (vii) trans-ferulic acid, EDC, HOBt, DIPEA, DMAP, DMF or DCM, rt.