Multi-step reaction with 11 steps
1.1: Bu3SnH / methanol / 2.5 h / 20 °C / Photolysis
2.1: 50 percent / pyridine / 20 °C
3.1: 100 percent / pyridine / 1 h / 0 - 20 °C
4.1: 100 percent / pyridine / 2 h / 0 - 20 °C
5.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C
6.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 72 h / 0 - 20 °C
7.1: CeCl3 / tetrahydrofuran / 4 h / -78 °C
7.2: 82 percent / tetrahydrofuran / 3 h / -78 °C
8.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
9.1: 99 percent / AlCl3 / diethyl ether / 1 h / 0 - 20 °C
10.1: 97 percent / pyridine / 0 - 20 °C
11.1: ozone / CH2Cl2 / 1 h / -78 °C
11.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C
With
pyridine; aluminium trichloride; cerium(III) chloride; ethanol; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
1.1: Reduction / 2.1: silylation / 3.1: silylation / 4.1: benzoylation / 5.1: desilylation / 6.1: Oxidation / 7.1: transmetallation / 7.2: Addition / 8.1: desilylation / 9.1: acetonidation / 10.1: Acetylation / 11.1: ozonolysis / 11.2: Reduction;
DOI:10.1021/ja962974q