Scheme 11.

The asymmetric synthesis of Dol-10 (1). Reagents and conditions: Please refer to Reference [98] for the synthesis of 133. (a) (1) TFA, DCM, 0 °C, 2 h; (2) HATU, HOAt, DIPEA, DCM, r.t., overnight, for two steps 85%; (b) (1) TFA, DCM, r.t., 2 h; (2) 40% HCHO, Na(BH₃)CN, CH₃CN, r.t., 18 h, for two steps 82%; (c) (1) HCl/dioxane, MeOH, 0 °C, 30 min; (2) HATU, HOAt, DIPEA, DCM, r.t., overnight, for two steps 80%; (d) (1) TFA, DCM, 0 °C, 2 h; (2) 136, Pd/C, H₂, MeOH, 2 h; (3) HATU, HOAt, DIPEA, DCM, r.t., 24 h, for three steps 60%.