Multi-step reaction with 19 steps
1: H2O
2: 97 percent / DCC; DMAP / CH2Cl2 / 0 °C
3: 74 percent / [RuCl2(=CHPh)(PCy3)(SIMes)] / CH2Cl2 / 40 °C
4: DIBALH / CH2Cl2 / -78 °C
5: toluene / 80 °C
6: imidazole / CH2Cl2
7: DIBALH / CH2Cl2 / -78 °C
8: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH2Cl2 / -20 °C
9: SO3*pyridine; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
10: 63 percent / LDA / diethyl ether / -78 °C
11: imidazole / CH2Cl2
12: DIBALH / CH2Cl2 / -78 °C
13: toluene / 80 °C
14: DIBALH / CH2Cl2 / -78 °C
15: 97 percent / BF3*OEt2 / methanol / 3 h / -78 - 0 °C
16: 91 percent / PPTS / CH2Cl2 / 1 h / 20 °C
17: 95 percent / L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH2Cl2 / 17 h / -40 °C
18: 93 percent / I2; PPh3; imidazole / CH2Cl2 / 3 h / 0 °C
19: 73 percent / NaBH3CN / tetrahydrofuran / 18 h / 50 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; pyridine-SO3 complex; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; water; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium diisopropyl amide;
4 A molecular sieve;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
5: Wittig reaction / 8: Sharpless asymmetric epoxidation / 13: Wittig reaction / 17: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e