Figure 2: Library synthesis from key building block 14.
From: Diversity-oriented synthesis as a tool for identifying new modulators of mitosis
(a) Cyclopentadiene, Rh2(OAc)4 (1 mol%), CH2Cl2; (b) m-CPBA, CH2Cl2; (c) OsO4 (2.5 mol%), NMO, acetone-H2O (9:1); (d) aldehyde/ketone, CSA (10 mol%), 3 Å molecular sieves, CH2Cl2; (e) SOCl2, CH2Cl2; (f) 2,6-lutidine, NMO, OsO4 (2.5 mol%), PhI(OAc)2, acetone-H2O (10:1), then dimethylamine, NaBH(OAc)3, CH2Cl2; (g) 2,6-lutidine, NMO, OsO4 (2.5 mol%), PhI(OAc)2, acetone-H2O (10:1), then primary amine, NaBH(OAc)3, CH2Cl2; (h) 2,6-lutidine, NMO, OsO4 (2.5 mol%), PhI(OAc)2, acetone-H2O (10:1), then NaBH4, MeOH; (i) alkene, Hoveyda–Grubbs (II) catalyst (10 mol%), ethylene, PhMe, 100 °C; (j) Pd(OAc)2 (10 mol%), PPh3 (15 mol%), 2 N K2CO3, PhMe, 90 °C.
