Scheme 1.

Synthetic procedures of methyl matrinate and matrinol derivatives. Reagents and conditions: (a) 5 N NaOH, reflux, 9 h, 6 N HCl, pH = 5–6; (b) 2 N MeOH/HCl, reflux, 2 h; (c) RBr, K₂CO₃, MeCN, r.t., overnight; (d) LiAlH₄, THF, r.t., 30 min; (e) R₂MgCl, THF, 0–25 °C, reflux, 2 h; (f) TsCl, CH₂Cl₂, TEA, 4-DMAP; (g) alkylmagnesium chloride, THF, reflux, 2 h