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. 2019 Dec 31;18(1):36. doi: 10.3390/md18010036

Scheme 2.

Scheme 2

Synthesis of Lissodendrin B. Reagent and conditions: (a) 4-methoxyphenylboronic acid, Pd(PPh3)4, CsF, toluene, H2O, 100 °C, 24 h, 82% (b) NIS, CH2Cl2, r.t., 4 h, 79%; (c) 4-methoxyphenylacetylene, Pd(PPh3)4, CuI, TEA, DMF, 80 °C, 8 h, 70%; (d) Ph3CCl, TEA, CH2Cl2, reflux, 4 h, 77%; (e) n-C4H9Li, TsN3, THF, −78 °C, 6 h, 46%; (f) Na2S⸱9H2O, CH3OH; r.t., 4 h, 69%; (g) (1) Ac2O, TEA, CH2Cl2, reflux, 4 h; (2) HCl, CH3OH, r.t., 4 h, 62%; (h) Hg(NO3)2, DMF, r.t., 4 h, 51%; (i) BBr3, CH2Cl2, r.t., 4 h, 66%; (j) concentrated H2SO4, CH3OH, H2O, reflux, 4 h, 51%.