Multi-step reaction with 15 steps
1.1: 95 percent / toluene / Heating
2.1: 99 percent / TiCl4 / CH2Cl2 / -78 - 20 °C
3.1: 92 percent / Na; NH3 / tetrahydrofuran; ethanol / -78 °C
4.1: 96 percent / DMAP / tetrahydrofuran
5.1: LiHMDS / tetrahydrofuran / -40 °C
5.2: 90 percent / tetrahydrofuran / -78 - 0 °C
6.1: 89 percent / LiOH; H2O / tetrahydrofuran
7.1: NEt3 / tetrahydrofuran
8.1: NaBH4 / methanol
9.1: 95 percent / NEt3; DMAP / CH2Cl2
10.1: 9-BBN / tetrahydrofuran
10.2: AsPh3; Cs2CO3; H2O / [Pd(dppf)Cl2] / dimethylformamide
11.1: TFA / CH2Cl2
12.1: K2CO3 / H2O
13.1: 86 percent / LiHMDS / tetrahydrofuran / -50 - 20 °C
14.1: 73 percent / ethanol
15.1: LiHMDS / tetrahydrofuran / 0 °C
15.2: 91 percent / [Cp2Zr(H)Cl] / tetrahydrofuran / 20 °C
With
dmap; lithium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; water; sodium; titanium tetrachloride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene;
1.1: Cyclization / 2.1: Ring cleavage / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Reduction / 9.1: Etherification / 10.1: Addition / 10.2: Alkylation / 11.1: Deacylation / 12.1: Michael reaction / 13.1: Condensation / 14.1: Cyclization / 15.1: Metallation / 15.2: Reduction;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I