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

Scheme 33.

Scheme 33

Synthesis of precursor 253, as reported by Rodríguez and Spur [113]. Reagents and conditions: i. Na2SO3, cat.CuI, K2CO3, H2O, 92%; ii. Jones reagent, acetone, 69%; iii.10%Me3SiCl, CH3OH, 2,2-dimethoxypropane, rt, 90%; iv. mCPBA, NaHCO3, CH2Cl2, 0 °C, 75%; v. (S,S)-(salen)Co (III)(OAc)catalyst, H2O, ether, 0 °C to rt, 45%; vi. TESCl, imidazole, Et3N, DMF, 0 °C to rt, 95%; vii. H2, Lindlar cat., hexane, 99%; viii. (COCl)2, DMSO, CH2Cl2, then Et3N, 83%; ix. Ph3P=CH–CHO, benzene, 70 °C, 43%; x. CrCl2, CHI3, THF, 0 °C, 69%.