Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / methanol / 0.33 h / 0 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
3.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere
3.2: -78 - 20 °C / Inert atmosphere
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 8 h / 20 °C / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere
8.1: methanol; hexane / 0.33 h / 0 °C / Inert atmosphere
9.1: toluene-4-sulfonic acid / methanol; water / 3 h / 45 °C / Inert atmosphere
10.1: zinc(II) chloride / water / 0.17 h / 120 °C / Microwave irradiation; Inert atmosphere
With
sodium chlorite; sodium tetrahydroborate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; zinc(II) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; pentane;
6.1: Dess-Martin oxidation / 7.1: Pinnick oxidation;
DOI:10.1021/ol301107m