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. 2024 Feb 2;14(7):4471–4481. doi: 10.1039/d3ra08485j

Scheme 1. Reagents and conditions: (a) TsCl, Et3N, Me3N·HCl, CH2Cl2 (99%); (b) HSCH2CH2OH, NaH, DMF, 100 °C (93%); (c) BnBr, NaH, DMF, 0 °C (32: 90%, 41: 99%); (d) HFIP, K2CO3, reflux (34: 96%, 42: 95%); (e) H2, Pd–C, 10% aq. TFA, 1,4-dioxane, 50 °C (26a: 94%, 28a: 93%); (f) 5% methanolic HCl, (26b: rt, 92%, 28b: 50 °C, 88%); (g) IRA-400J (Cl form), CH3OH, rt (26c: 93%, 28c: 87%, 39: 98%); (h) HSCH2CH2OH, K2CO3, C2H5OH, reflux (99%); (i) HBF4·(C2H5)2O, CH2Cl2, −78 °C (71%); (j) H2, Pd–C, CH3OH, rt (89%).

Scheme 1