Multi-step reaction with 13 steps
1.1: 88 percent / Jones reagent / acetone / 0 °C
2.1: (R)-(-)-BINAL-H / tetrahydrofuran / 17 h / -100 - -85 °C
3.1: 97 percent / H2 / Pd/BaSO4 / methanol / 3 h / 20 °C / 760 Torr
4.1: pyridine / CH2Cl2 / 1 h / 0 °C
5.1: 445 mg / (n-Bu)4NCl / CH2Cl2 / 12 h / 0 - 23 °C
6.1: Me2BBr / CH2Cl2 / 2.1 h / -78 - 23 °C
7.1: 203 mg / i-Pr2NEt; AgOTf / CH2Cl2 / 3 h / 0 - 23 °C
8.1: BCl3 / CH2Cl2 / 0.17 h / -78 °C
9.1: BCl3 / CH2Cl2 / 0.58 h / -78 - 23 °C
10.1: 30 mg / TBAF / tetrahydrofuran / 4 h / 0 - 23 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 0.42 h / 23 °C
12.1: 31 mg / tetrahydrofuran / 1 h / -78 - 23 °C
13.1: Co2(CO)8 / diethyl ether / 2 h / -23 - 0 °C
13.2: Tf2O / CH2Cl2 / 2 h / -78 - -5 °C
13.3: (NH4)2Ce(NO3)6 / acetone / 23 °C
With
pyridine; jones reagent; dicobalt octacarbonyl; dimethylboron bromide; (R)-(-)-BINAL-H; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; silver trifluoromethanesulfonate; boron trichloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine;
Pd-BaSO4;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
1.1: Jones oxidation / 2.1: Reduction / 3.1: Hydrogenation / 4.1: Esterification / 5.1: Substitution / 6.1: Bromination / 7.1: Substitution / 8.1: Substitution / 9.1: Prins cyclization / 10.1: desilylation / 11.1: Dess-Martin oxidation / 12.1: Addition / 13.1: complexation / 13.2: Dehydration / 13.3: decomplexation;
DOI:10.1021/ja964080b