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. Author manuscript; available in PMC: 2015 Dec 22.
Published in final edited form as: Science. 2015 Mar 13;347(6227):1221–1226. doi: 10.1126/science.aaa5414

Fig. 3. Automated synthesis of ratanhine derivatives.

Fig. 3

Conditions: deprotection – NaOH, THF:H2O; coupling – cycle 1: Pd(OAc)2, SPhos, K2CO3, THF, 55 °C, 16h. cycle 2: Pd(OAc)2, XPhos, K3PO4, THF, 55 °C, 14 h. cycle 3: Pd(OAc)2, SPhos, K3PO4, THF, 55 °C, 24 h; purification – SiO2, MeOH:Et2O; THF. All protecting groups other than MIDA (R = TIPS, TBDPSE, TMSE, or Bz) were successfully removed in a separate step (24).