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Fig. 1 | BMC Research Notes

Fig. 1

From: Synthesis of aromatic lactone analogues of Lipoxin A4

Fig. 1

A Key synthetic strategies towards the target lactones. B Synthesis of key intermediate 7; a) 2,2-dimethoxypropane, DMF, MS 5 Å, 0 °C, 3 h, then rt overnight, 41%; b) Ph3PCHCO2Et, benzoic acid, toluene, reflux, 87%; c) H2 (1 atm), Pd/C, EtOAc, rt, 93%; d) SO3-Pyr, Et3N/DMSO, DCM, rt, 87%. C Synthesis of key phosphonium salts 12 and 17; e) Heptanoyl chloride, AlCl3, DCM, 0 °C, r.t, 30 min – 1 h, 73%; f) NBS, THF, H2O, hv, r.t, 83%; g) PPh3, acetone, reflux, 3 h, 82%. h) Heptyl bromide, K2CO3, CH3CN, 24 h, reflux, 72%, or; KOH, EtOH, H2O, 24 h, reflux, 76%; i) NBS, Bz2O2, DCM, reflux, 9 h, 48%. j) = g), 72%

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