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. 2022 Mar 3;27(5):1677. doi: 10.3390/molecules27051677

Scheme 14.

Scheme 14

Preparation of the building blocks for the synthesis of RvD4, as reported by Serhan et al. [90]. (A). Synthesis of C10–C13 fragment; (B). Preparation of C14-C22 fragment; (C). Synthesis of Sonogashira cross-coupling partner 106. Reagents and conditions: (A). i. I2, imidazole, PPh3, CH2Cl2,4h; ii. PPh3, MeCN, reflux, 12 h; (B). i. cat.PTSA-H2O, DHP, 5 min; ii. But-1-yne, nBuLi, BF3.Et2O, THF, 3 h; iv. TBSCl, imidazole, DMF, 3 h; Ni (OAc)2.4H2O, NaBH4, H2N(CH2)2NH2, H2, EtOH, 12 h; v. MgBr2, Et2O, 4 h; vi. (COCl)2, DMSO, Et3N, CH2Cl2, 0.5 h; vii. Ph3P=CHCHO, Net3, PhH, 12 h; (C). i. NaHMDS, THF, −78 °C, 3 h; ii. TBAF, THF, 40 °C, 48 h.